Whoops and Wins: the lessons I learned on “leading-up”

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In my last post, I shared “what’s the best approach to leading up?” And as a follow-up, today I am sharing ways I’ve done this well and ways I have screwed it up.

And here’s why I’m continuing this conversation: any kind of leadership is often accompanied by the anxiety of making decisions that require taking the first step. And the anxiety of decision-making while “leading-up” soars to an entirely new level when someone is intentionally or unintentionally blocking you from taking that first step in the right direction.

I want you to know you can make the wrong decision (the whoops) and still keep leading-up just as easy as when you make the right decisions (the wins).

Whoops: I was just hired in my first significant role helping to create community for a big a church and I was really excited about what I was doing. I attended a community-life conference, read a few books, and quickly felt ready to change the strategic direction of this ministry area of our church. So, I set up a time to meet with the senior leader and pitch my idea. My first mistake was that I came into the meeting with a strong sense of urgency (subtle was not in my vocabulary then), and while my thoughts may have been good, my timing was off. I was new to staff, didn’t have as much relational equity with the leaders around me, and needed to do more listening and learning than talking and making pitches. The second mistake was having a myopic view. If I had taken time to look, listen, and learn, I would have seen there were bigger issues that needed to be addressed by the executive leadership team before they got to my brilliant idea.

Win: Leading up in a large organization can be difficult. My second role was at an even-larger-church than the first, and within a few weeks on campus, I couldn’t help but notice just how many staff members and volunteers weren’t being seen. There were a lot of silos, lack of vision for the main campus where I was located, and a significant lack of care at every level of our community: staff, volunteers, and people attending our church. Inspired by a talk I heard by a pastor in Atlanta, Georgia, I started to do what only I could do. If I wanted to see change, I knew I needed to make that change happen for the teams of people in my care. But it just didn’t seem like enough. I was making one tiny dent in a massive organization that was losing people left and right. And I didn’t have easy access to the decision-makers–most of whom defaulted to one senior leader. So, I took a risk to email that leader with a few questions and observations I had made during my first two years on staff. That email created a conversation with him, which eventually led to some big changes at the main campus of our church. I don’t think this approach would have worked if I tried to talk to the senior leader right after he was done teaching on Sunday, or trying to catch him in the parking lot as he exited his car. Sending an email when I didn’t have access to a face-to-face conversation with that leader gave me time to carefully and kindly express my thoughts, and gave him time to respond rather than react.

Whoops: As a campus pastor of a relatively large church campus, I had the privilege of leading, but not always being in charge. At one point, all of our campuses participated in a Giving Challenge where people would give their time and resources to things happening in the community. I loved the idea, but I was frustrated that this opportunity only happened a couple times during the year, and frustrated that the campus pastors didn’t always have a say in the ways we cared for our communities. Couldn’t we make everyday a giving challenge wherever we were? Wasn’t that just part of being human? Fast-forward a few months, and I was approached by a local organization in our campus community that needed help getting backpacks and supplies for kids as they returned to school. Within a matter of days, we had a solid volunteer team in place from our campus and we packed a school bus full of supplies for those kids. It was awesome! But the only problem was I didn’t let any of the other campus pastors or our senior leadership team know I was doing it. I did what’s called an “end-around.” The truth is, I knew it would take a while for this idea to get approved and there was a risk of denial, so I just did it, anyway. In doing so I broke the trust of some of my leadership peers which made it harder to lead-up with them in the future.

Win: As you can tell from my last story, there was a bit of tension for me leading at a church campus in a local community and yet most of the decisions were made by a central team at the main campus miles away. There were things the central team didn’t know or understand about our campus. One of those things being that we had 5 gatherings on Sundays, and no one from the central team had ever been on staff at a campus where there were 5 gatherings in 1 day. Not to mention that the campus where I led had a weekend attendance of almost 2000 and a staff of 5 people. The ratios at the other campuses were about 1 staff person for every 200 attendees, and we were 1 staff person for every 400 attendees. Our worship leader not only had to recruit, develop, and lead volunteer worship teams for 5 gatherings on Sundays, but also needed to lead a mid-week rehearsal, patch all of their own cables on the stage without extra production staff to do it for them, do pastoral care alongside the campus pastor (me), attend team meetings, and so on. This was getting to be too much for both of us. So, in my 1-on-1 conversations with the worship leader, we worked on a way to request members of the central team come to our campus and fill in for the leader a few weekends a month. This decision created crucial conversations between our campus and the central team about the reality of all that we were carrying and how they could better support other campuses in general. In this case, I learned that sometimes the best type of leading up is giving people an opportunity to step into your shoes and see things from your perspective.

Whoops: Here’s the thing most of us learn the hard way: we can have the right idea at the right time, but it might be the wrong place. I’ll never forget the day I was sitting in a leadership team meeting where the senior leader was sharing thoughts monologue-style. It really wasn’t a “meeting,” because my view of a meeting is a place where people exchange thoughts and wrestle with ideas. I was hoping to be a part of the dialogue, rather than being subjected to this monologue. And at one point in this “meeting,” something was shared that seemed like a horrible idea to me. I waited for the senior leader to take a breath and then I challenged his decision in front of everyone. Now, I am all for challenging ideas and wrestling with decisions in meetings, but looking back, this was not the right place. While some of my co-workers thought it was admirable that I had the courage to challenge, it was a bad approach because it wasn’t the place to be heard. And the truth was, this senior leader was okay to be challenged, but not in front of others. It took me a while to rebuild trust and get to the place where he asked for my opinion before I had a chance to be heard.

Win: Ironically, the same leader who didn’t like to be challenged publicly was okay to publicly challenge others. And I was caught in the cross-fire of these challenges on occasion, which was never fun. Leading-up in these instances looked like requesting 1-on-1 meetings after the team meetings where I could ask questions to understand where he was coming from. At first I thought I needed so many 1-on-1 conversations because this particular person and I just kept missing each other . . . because we weren’t taking the time to look, listen, or learn from one another. And then I realized we were missing each other because we had really different values. After a few years of trying to understand where he was coming from, and leading up in every way I could imagine, I realized it was time for what Dr. Henry Cloud calls a “necessary ending.” What I first thought was The ultimate win was that this dance in leadership conversations revealed a necessary ending and required confidence to step away from the organization.

THE LESSON: Leading-up will teach you a lot of lessons about yourself, the leaders you work with, and your organization, including the “wins” and the “whoops.” So learn to embrace it all and make the best choice you can whenever you have the opportunity to exercise that “leading-up” muscle.

YOUR TURN: What kinds of “wins” and “whoops” lessons have you learned in leading-up?

What’s the best approach to “leading up”?

A few weeks ago, I stood at the end of a grass strip runway wearing a bright yellow vest and muttering out loud, “What the hell is this pilot doing?!” He was coming in hot and fast for a landing and I wasn’t sure whether to run away or take cover on the ground.

My in-laws were hosting a “fly-in” on their property in West Virginia that weekend. What’s a “fly-in” you ask? Think of it like a family reunion where everyone meets up from all over the MidWest and pulls up in their own tiny airplane rather than the family car. Pilots flew in just for the day from Michigan, Connecticut, Ohio, Pennsylvania, North Carolina and everywhere in-between. It’s the fair-weather-weekend thing to do for small airplane pilots, just like bikers gather for weekend rides. Beth’s parents have a house that sits on the side of a mountain deep in the woods, but at the bottom of the mountain is the Cheat River. And in the middle of that river is a 30-acre island big enough for not just one, but two airplane landing strips.

Landing on the island is tricky because it sits in a deep valley that twists and turns along with the river. The day of the fly-in I saw planes come for landing in too fast, too slow, and too high, but thankfully never too low. Some pilots had to circle high in the air for a few laps in order to calculate their best landing approach. Even with a careful eye and the best intentions, a few pilots realized at the last minute they were going too fast or flying too high for a good landing, so they had to throttle the engine, pull up, and come back around to try their approach again. Or they all arrived in the air space around the island at the same time and got stuck in a holding pattern until they were directed to land one at a time.

Now, I am not a pilot but I’ve learned a few things from being in the cockpit of a small airplane on several occasions, and from standing on the end of a runway directing small airplane traffic. And here’s what I’ve realized: having the right approach is key for landing a plane and for leading up.

Leading up can be very tricky to do, which is why I often have leaders ask me, “What’s the best approach to leading up?” or simply, “How do I lead up?”

Considering your approach

Just like landing a plane, with leading up you have to be really intentional, thoughtful, and humble when considering your approach. I once needed to tell a senior leader about something they needed to do differently and my manager coached me to approach the conversation like a chess game. “you will say this, and then they will say this, and then you can make this point, and they will react this way, when then you can…” I made the first three moves and realized really quick it was not working, so I changed my approach and simply said, “can I be honest with you about a few things that I am struggling with?” That approach led to a great leading up moment.

Getting stuck in a holding pattern

Team leaders also like to motivate, inspire, and direct from out front, but they often get stuck in a holding pattern with other people who are on the org chart in front of them. This kind of holding pattern–due to a boss, a board of directors, the CEO, or even a parent–causes the best of leaders to lose momentum, feel stuck, or even question their role or responsibilities. Maybe there’s an idea, a clear vision, an old concern, a new tool, an potential proposal, or something that seems necessary for sake of the organization but you can’t implement it because it needs approval from your senior leader or the person who’s “in charge”. Sound familiar? Countless times I’ve listened to the stories of leaders who were inspired by outside ideas gathered at a conference, but then discouraged because they knew the idea would not be welcomed by their boss. Or from leaders who see a blindspot in their organization, but they are afraid to share it for fear of being dismissed by their boss. If you feel stuck in this kind of leadership holding pattern, you’re not alone.

Here are a few Q’s to ask as you consider the best approach to leading up without getting stuck in a holding pattern:

  • Is this the best timing? Look for the best opportunities to approach a conversation. Some times you might have the right message but it might be the wrong time to have the conversation. If you are wondering ask others that are closest to this leader on when are the best times to connect with them, or even ask them when the best time is. This allows them to know you would like to discuss something. Ask yourself, is this a short or long approach? If you are leading up with something that might shift the leader or organization in a significant direction you might consider a series of strategic approaches.

  • Who am I dealing with? Every leader is different and will require a different approach. Beth and I realized with our oldest son it was better to have side-by-side honest conversations rather than the intensity of face-to-face. We would go for a walk together which felt way less intimidating to him. With our youngest son the best approach was to engage in an activity with him while having conversations. Some of the best conversations we have had have been when throwing a ball around. You might not play catch with your boss but there might be a more effective approach for them to hear you.

  • What’s the best location? Your approach to leading up might not work because you are in the wrong setting. Consider helping your leader visualize an idea by having a conversation in a different context. Sometimes the leader is too busy to schedule a meeting but walking into the office from the parking lot might be a good approach, or meeting in a nearby spot to talk a walk instead of sitting down in an office might spark a different kind of conversation.

  • What questions do I need to ask? Asking intentional, thoughtful questions is a great way of leading up with a learning approach. Asking questions like: Have you considered….? Would you mind if I reflect what I have been seeing lately? Could you help me understand why…..? How do you see us… ? Questions create connection, allow you to hear their perspective, give permission to participate, and show what things are important to you.

  • How can I put myself in their shoes? You might want to ask this question first. This question helps create empathy with your leader. Too often we think that leaders have all the answers, or have experience with what they are leading. When I put myself in their shoes I realize they might be scared to death of the decision that is in front of them but pretending to hold it all together. Your leader might not have ever led an organization like this, at this size, with certain people, or during this time. Putting yourself in their shoes helps understand what approach you might need to take and allows you to have grace at the same time.

In part 2 of “leading up”, I will share a few specific examples of where I personally have led up well and where I have missed the landing with a bad approach.

I would love to hear from you! Where have you led up well with the right approach, and how have you missed the landing with a bad approach?

Transition: factors & fears

(This is part 2 to my last post: Is it time to transition?)

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At age 26, I was living my “dream” life. I had the type of teaching and coaching position I dreamed about at a well-known high school in the Philly suburbs. Beth was working nearby in higher education, and we were going on 3 years of marriage. But we also sensed a growing nudge and an unshakable curiosity that there was something else, another version of our “dream” life, for us to consider. Since we were both in education, we explored the possibility of working and teaching at an international school. One thing led to another, and we found ourselves signed up for a 2-year volunteer program with an international missions organization. We were enamored with that particular program because it meant teaching organized sports in a remote island village community in Africa. Up until that point in our lives, Beth and I both spent a fair amount of our lives playing sports, teaching and coaching. So, it sounded like a perfect fit for us. We quit our jobs, joined a team of 6 others, and headed to the island where we would spend the next two years of our lives (or so we thought . . . keep reading). At that point, we were eager to step into what was called “full-time ministry.”

I’m not going to lie. There were some exciting factors about this big transition: living in a new place, learning a new language, taking theology/missiology courses, being with a team we loved, teaching sports we loved, traveling all over East Africa, learning to live a simple life, and so on.

But there were also a ton of fears:

  • What if we’re not good at this?
  • What if we don’t make enough money to make this work?
  • What’s my/our purpose in this new place?
  • What if our marriage struggles as a result of this move?
  • Will we find a place to live?
  • Will we get along with our teammates?
  • Will we find new friends?
  • Are we ridiculous to give up good jobs here in the US?
  • What will others think of us?
  • Where is God in all of this?
  • What if this doesn’t work out?

Fear sometimes helps us ask really good questions–questions that accompany most major transitions. But fear can also paralyze us from taking the best next step.

For Beth and I, a few of these fears became our reality. After almost six months of living in Africa, we found ourselves back in the US with no money, no car, no jobs, a broken dream, a strained marriage, a confused relationship with God, and expecting our first child (the reason we had to leave where we were living). There were days it felt like we traded our dream of living overseas in for a nightmare.

We eventually recovered from this experience thanks to a supportive family, a loving community, a trained counselor, and a church where we could hide and heal for some time.

Plot Twist

Fast-forward five years, and I had another “dream” teaching/coaching position at a high school near Lancaster, PA. And then, I had another opportunity to jump back into “full-time ministry.” The church we were attending at the time asked if I would consider a position as the Community Life Pastor. So, once again, we processed many of the questions I wrote in my previous post (Is it time to transition?). We had many of the same fears and questions when we were on our way to Africa, maybe even more so this time because of the hurt and frustration of the dream we lost there. But we still had a sense this was the best next step for me to say yes to working at our church.

(Note: I use quotes around “full-time ministry” because I think wherever we are, whatever we do is full-time ministry)

But I was shocked when I starting sharing this news with my peers, the teachers and friends at the school where I was working. I thought they were be excited that I was joining the staff at my church, instead they looked at me like I was crazy. Their responses: “Why would you give this up?” “Who wouldn’t want to be a P.E. teacher and coach?” “You get paid to play games for a living! Why would you let go of that?” On the outside my enthusiasm took a small hit, but on the inside I still knew this was my next step.

The response I remember most clearly was the co-worker who said, “Wow. I’m actually jealous of you. I wish I could leave and go do something that I was really passionate about, but I am 10 years away from a really good retirement and I make decent money. I hate my job but I can’t leave because I have too much going on here.” This stuck with me for years. And I couldn’t help but feel bad for this guy because perhaps he was missing out on something more for his life. It made me wonder how many people settle for financial safety or job security and miss out on opportunities they are well-suited for and experiences they would love.

Beth and I would go on to make two more crucial transitions in the years ahead, a move to Southern California and then to South Bend, Indiana.

Transitions are like Subways

I’ve coached and mentored a lot of people through their own transitions, and in almost every single story is a moment of paralysis because of fears and “what if’s.” They’ve also somehow convinced themselves that there is only one “right” answer to their transition, believing “it’s either ‘this’ or ‘that.'”

My life experiences taught me that transitions are like subways: if you miss your train, there will be another one that approaches in the future. If you get on the subway heading the wrong direction, you can always hop off and get on another one heading back in the direction you came from, and you’ll even have a better sense of direction because of it.

Hopping on one subway train of opportunity and moving towards living the life of your dreams might not pay well. It might require moving or letting go of some hard things. It might even require you to sacrifice your power, prestige, or position. But you’re not alone. There are countless others wondering and doing the same. And if you make a decision that doesn’t go well, you can always make a different decision. I’m convinced that our transitions, both good and hard, shape our lives in ways we can’t experience any other way.

Turning Points & Transitions

In 2017, Beth and I had the opportunity to go through the Paterson Center LifePlan experience. At one point over the 3-day experience, our guide, Doug, led us through a Turning Points exercise. Beth and I mapped out our life together in 10-year increments and marked our defining moments as individuals and as a couple. There were a number of high and low points of our lives together, and a number of life transitions along the way. Then we ranked the most-defining moments as “turning points” in our lives.

Here are few things we learned by looking at our turning points:

  1. When Beth and I commit to something, we are all in.
  2. We have had everything we’ve ever needed even in the midst of change, thanks be to God.
  3. It’s a strong value for us to live in the community wherever we work.
  4. Our small family of 4 is free to look different and make different choices than our extended families.
  5. I’m a relational leader who flourishes in an empowering & affirming culture
  6. I have so much more to offer then my early story has told me (Beth).
  7. Our transitions represent opportunities and open doors. The choice to leave previous environments has been more about discovery vs. abandonment. It was more about what we were running to instead of running from something.
  8. “Ministry” will always be who we are wherever we are.
  9. We need a safe & nourishing community of friends & mentors, and will seek these people out in every place we live.
  10. We are values-driven as individuals, as a couple, and as a family.

Twenty years ago, I would never have imagined that I would be an Executive Pastor living in South Bend, Indiana. I would have told you I’d still be a Phys. Ed. teacher or a high school principal. While those are noble and respectable roles, those roles were no longer meant for me. But . . .

It’s not about what we do, it’s about how we live our lives while we do what we do.

For me, not making a transition out of teaching would have been a decision guided by fear. And even though some of our transitions were hard and a few of my fears came true in our transition to Africa and during our time in California, I wouldn’t take back those choices and transitions. I wouldn’t take back what we learned about God, ourselves, and each other as a result of those transitions. There were things we needed to learn, people we needed to meet, and experiences we needed to have.

Your Turn:

If you’re in the middle of a transition and full of questions, factors or fears, I believe the best way to overcome worry for wherever you are or doubt about wherever you are headed is to look back and see where you’ve come from. That’s why I recommend this Turning Points exercise.

Start with a blank piece of paper, online or in person. Make a row of columns from left to right, one for every decade of your life. (note: if you’re still in your 20’s, make a column for every 5 years of your life). Next, write down all the defining moments (highs and lows) of your life in each decade / column. Then rank your top 10 defining moments with numbers 1-10. Out of these top 10, which events created a turning point for you? Perhaps it’s only 4 or 5 out of the 10 events, or maybe it’s all of them.

Now answer this series of questions and journal your answers:

What did you learn about yourself, your family, God, your community, and your vocation as a result of each one of those turning points?

And when you’re done with this exercise, make a list of the factors involved in making this transition. I’ve found that’s helpful, too.

As always, I’d love to hear from you if you’re up for sharing about your own transition or turning points experience.

Is it time to transition?

Questions to ask yourself and others when considering a transition.

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Transitions are a natural part of life, but not many people pause to think about how to transition well. 

Cue the people who start their “dream job” only to exit a few months later because the transition was not done well by their organization, or they didn’t quite think it through as individuals.

And by “transitions” I mean starting a new job, leaving a job, changing teams, moving to a new location for the same job . . . and everything in between.

Beth and I have made a few big transitions in life: moving across the globe once and across the country twice, new jobs, and new careers. And we’ve been pretty transparent about those transitions, so I get asked this question a lot:

How do I  know when it is time to transition, and how do I transition well? 

Before I answer this question, I can tell you what keeps people from making a necessary transition: FEAR (but I’ll share more about that in my next post).

Transition Questions:

Here are a few categories and questions I’ve processed on my own and with others regarding transitions: 


(and if “God” is a word that doesn’t work for you, that’s ok! Replace it with “a higher-power”)

1. What do you sense God is saying and how is that leading you?

2. What do those who know you best think about a change? (People can be a voice of God in our lives)


1. Why a change?

2. Why a change now?

3. Are you running from something or to something in this transition? Do you know?


1. Why is this a good time to consider a move?

2. Why is it a bad time to consider a move?

3. Is your extended family a support system for you? If not, who is a support for you? And what support do you need?


1. What is one word you would use to describe where you are right now?

2. What do you enjoy? What is giving you life?

3. What is draining you?

4. What has changed? What’s stayed the same?


1. What direction are you heading? Where do you want to land?

2. What are your non-negotiables? Make a list.

(Examples: Values/Location/Culture/Role/Finances)

3. If you were to create an ideal job description what would it be? How does this compare to where you are, and the opportunity ahead?

4. Who needs to walk alongside you during this process?

The Challenge of Transition

Transitions can be difficult because they involve people, place, timing, families, schools, communities, housing, finances, skills, and deep rooted history. Just because a transition could be difficult, doesn’t mean it isn’t the best next step. It just means you need to be thoughtful and intentional about how you make the transition. 

If you are thinking about transitioning and these questions are helpful to you, then I would love to hear from you.

Can a meeting be efficient & engaging at the same time?

3 Questions that will cut your meeting time in half but double your engagement.

Have you ever walked away from a meeting and said to yourself or someone else, “Well, that was a waste of time! We just met for two hours and…. “

  • I heard the same person talking the entire time.”
  • We didn’t talk about anything important or helpful.”
  • I am not sure what just happened in there.”
  • We didn’t even get to talk about the most important thing!”
  • “I need a drink.”

Facilitating a good meeting is like putting together IKEA furniture . . . it goes a lot better if you have a step-by-step plan, and the right tools for the job. Lose that little guide or your tool, and your HEMNES is not going to look so good. Am I right?!

I’ve talked to a lot of leaders, who have no guide and are uncertain about which tools to use, who ask me, “How can I run an efficient and engaging meeting? Is it even possible to do both at the same time?

Death By Meeting

Years ago I was introduced to Patrick Lencioni’s book, Death by Meeting, which is an excellent guide to creating engaging and effective meetings. I highly recommend it. Pat talks about how he structures a few different kinds of meetings. And here’s the one that’s made the most significant breakthrough for me.

Weekly Tactical Meetings: According to Pat, the team meeting starts by having everyone go around the room and each person has 60 seconds to share 2 or 3 things that are on the top of their list. I learned from a former team leader who adapted this approach that this works best this way: each team member shares three things we were working on in a quick verbal or written meeting brief, and no one talks about their own list unless they are asked a question about it by another team leader. This made our meetings more efficient but a new problem emerged for me. 

The Problem: As I began to lead meetings using this approach, I noticed I knew what everyone was working on, but I had no idea what was going on in their lives. This really hit me hard when I found out way too late that my administrative assistant’s sister had cancer. 

A few questions emerged for me as I started to rethink my approach to weekly tactical team meetings:

How can I work so closely with someone and not know anything about them? How am I leading at a church of all places and we don’t know what is going on in each other’s lives.

That’s when the 3-2-1 idea came to life for me. 

My 3-2-1 Approach: a Practical Tool to Guide Your Meetings

The past number of years I’ve asked the teams I’ve led to submit their 3-2-1 lists prior to our team meeting via email or slack–whichever communication method each team uses the most. They reply just to me if it’s email, and I share the list ahead of our team meeting, or if it’s something like Slack, then they “reply all.” And those 3-2-1’s go something like this:

  • 3 things you are working on
  • 2 things happening in life
  • 1 work-related goal you have for the week

Here is the latest 3-2-1 I shared with my team:

Our team uses Slack and posts on our team meeting thread their 3-2-1 prior to the start of the meeting. At the start to every meeting we take about 30 minutes to ask each other questions about our 3-2-1’s. And you’d be surprise at what comes up.

Here is what I love about this: 

  • People only talk about what they are asked about. Too often in meetings, someone shares about something that nobody cares about or doesn’t impact their area. This helps your team ask questions and create intentional connections.
  • Team leaders have shared that this helps their team really focus on what they are working on and goals each person has for the week. 
  • If someone writes the same thing on what they are working on week after week after week, this creates a coaching conversation between me and them re: what’s stuck and why. 
  • If there is something I think should be on their top three and it’s missing from their list, this also creates a coaching conversation.
  • This allows people to follow up with each other outside of a meeting on other questions or things going on in their lives.
  • This creates written accountability for each person on the team, me included.
  • Last but not least. I find most people ask questions about the 2 things going on in life more than the goals or things we’re working on, and I actually think that’s GREAT! As a team leader I am so glad I and the rest of the team are not missing out on what is happening in people’s lives. This creates connection, trust, and allows the team to lean into one another.

Let me know if you try this 3-2-1 approach! I would love to hear about your experience. Comment below or shoot me a message at teamgraybill@gmail.com.

How to structure a 1-on-1 conversation?

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In order for any relationship to grow there needs to be consistent and clear communication. This can make or break a relationship. Many organizations are so focused on communicating with their customers or clients, they don’t stop to think about it when it comes to their employees. 

As a leader, a manager, even as a coach, I believe 1-on-1 meetings are essential for the growth of your team, as well as the health of your organization. Which is why one of the most common questions I have been asked is:

How do you structure your 1-on-1 meetings? 

First, ask yourself: why am I creating this 1-on-1? These conversations are not meant to be a top-down, one-directional experience. If this is your perspective, you are missing a lot of potential growth opportunities all around–for yourself, your teammates, and your organization. 

Second, start to see 1-on-1’s as essential to your communication pipeline. These conversations are a great place to cast vision, share information, do some coaching, and exchange personal reflection with members of your team. 

Here are a few things to keep in mind when starting 1-on-1 conversations:

  • Rhythm: Consistency is key. The rhythm that works best for me and my team is every other week for 60-90 minutes at a time. If someone needs more support in a particular season, I will make it once a week. (I’ve typically done this with interns or with individuals who are struggling in areas of performance management). Every other week creates enough space to have purposeful and focused conversation without getting lost in the weeds of daily details. Now, you may be wondering why you should have a 1-on-1 because you have a team member who constantly stands outside your door, asking questions or wanting to share their latest thought. This is exactly why you need to have a 1-on-1! From my experience, I’ve found that asking that talkative team member if the conversation can wait until your 1-on-1 is helpful for managing time. Sometimes what they have to say is urgent, and that’s okay. But if it’s not urgent and they have a tendency to hijack your day with conversation, you can now politely tell them their updates or random questions can wait until your next 1-on-1 meeting. (Hear the coaching that happens even in those little conversations?) This prioritizes your time, and helps them prioritize their time, too.
  • Setting: Find a place that feels safe & comfortable for conversation. Remove barriers that create leadership distance. Get out from behind your desk and sit in more of a casual seating arrangement or in a neutral space outside your office. Depending on your workplace policies, meeting in a common area or conference room maybe be helpful as long as the conversation can be confidential as needed. And turn off phone or email notifications, if possible, to give your undivided attention. A team member should feel safe in every interaction they have with you , but especially when you are meeting 1-on-1.
  • Intentionality: Be intentional about your time together. Communicate the expectation and flow of conversation ahead of time. And don’t have meetings just to have meetings. Bring intentionality to your conversation and you will be surprised how much it impacts their growth and development.

Now it’s time to get started with the actual conversation.

Here are 5 questions I typically ask in each 1-on-1, and I include these in the calendar invitation so my teammates know what to expect. I also make sure they know this is their time, too, and it’s okay to talk about other things that are important to them, even if these items are not on my list of questions: 

  1. What are you celebrating?
    • People have a hard time bragging on themselves. This gives them an opportunity for them to share what they are doing well without feeling like they are being self-centered. 
    • This is also an opportunity for you as a leader to call out what you see them doing well. 
  2. What needs attention?
    • As a manager you might know what needs attention in their world, but do they. This creates an honest conversation about what is most important right now.
  3. What are tensions?
    • This gives space for them to share the tensions they are facing. And you might be surprised! It could be tension with a coworker, with a task, or even something personal they are facing at home which is impacting their work. 
    • This is also an opportunity for you as a leader to name the tensions you might be feeling or experiencing with this individual, and have an open, honest conversation about it. 
  4. What are questions?
    • This gets at the questions they have as well as the questions they get from others. Often times, these questions reveal a communication gap, which can help you redirect what needs to be communicated. I have been amazed at things I thought myself or our organization communicated well, only to find out we were missing a few important pieces.  
  5. How can I better support you? 
    • This is a tough question to ask, because you need to be willing to be big enough to hear the honest answer. If you want a team member to be open to coaching then you need to be open to coaching yourself. Asking this question and owning the answer will make you a better leader. I asked this question at every 1-on-1 I had with a former boss, and never did he reciprocate the question. My sense is he never asked me because he was too afraid of the answer he was going to get. Also, asking how you can support someone is different than asking if you can help them. Support communicates that you will support them while they do the tasks, and help communicates you will do the tasks for them. A small but significant difference.

If you’re just starting your 1-on-1 rhythm or you’re switching things up and trying something new, I’d love to hear from you. Let me know what’s working and not working, or feel free to ask more questions about my 1-on-1 rhythm @matthewgraybill

Strategic Planning: Why are they being so quiet?

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Have you ever been in a meeting where you needed to interrupt others just to get your idea shared, or tuned out because it’s always the same people talking? Me too. What’s worse than participating in that kind of meeting, is leading that meeting. Especially when you have a few quiet voices and want to make sure they feel seen and heard, too.

I often get asked by other leaders: How can I make sure everyone’s voice is heard when we are doing strategic planning?

The answer is not as simple as just asking the quiet person in the room what they are thinking. I have found there are a few common reasons why someone is quiet in a meeting.


  1. They don’t think what they have to say matters. (this might be their insecurities but it could also be a leader who doesn’t value other people’s ideas)
  2. They might be more of an introvert, and they’re not going to “fight” to be heard. 
  3. They may need time to process what is being discussed before they share something out loud.
  4. They think or feel like the decision has already been made.

If you want to hear everyone’s voice during a meeting, you need to first ask yourself, “Why”? Is it that you really value their thoughts and opinions, or do you just want everyone to agree with you and make people feel like they participated? Let’s be real. Leaders typically know where they want to go in conversation, so it can be difficult to honestly ask your self that question and allow other people to put their hand on the steering wheel.

Much of what goes into creating space for all of the voices in the room happens before the meeting. It involves trust that comes from valuing everyone’s thoughts and ideas. It involves 1-on-1 meetings asking people what they honestly think, and then putting into practice the helpful feedback you receive.

I have learned that in order to hear everyone’s voice I need to send a few of the questions we are going to process ahead of time. This gives individuals on my team time to think and process on their own before we all process ideas together.

If you really want some great ideas to guide your strategic planning, allow people to simmer on their thoughts for a while. Not everyone operates like an insta-pot. Some people are more like crockpots, they need time. 

EXAMPLE: Here’s what I mean . . .

Recently our team did a strategic planning day centered around a few questions. I sent those questions and discussion items out ahead of time because I really wanted our team to guide the planning process. I knew they had a better chance of participation if I gave them extra time to think about the questions.

Then we got together and started by writing answers to the questions on a creative map, rather than jumping straight into conversation. I drew a pathway with some “artistic” features that gave our team time to brainstorm without even speaking a word to each other. (Note: drawing images that help guide conversation, like the one below, bring life to the meeting, and it’s better than a boring sheet of paper)

First, I asked everyone to write down their thoughts on the sheets of paper. Then, I asked people to read what others wrote and see if that spurred on additional thoughts for them. They had 10 more minutes to revisit their own answers. In just a short amount of time, we had all of the pages covered with great thoughts and ideas, without saying a word.

A lot of threats and frustrations were eliminated in this exercise. No one had to raise their voice or talk over others to be heard. No one had to worry if what they said was articulate. No names were added to the comments so unless someone memorized everyone else’s handwriting, no one knew exactly who wrote what. And it took minutes, not hours, to go around the room. All the thoughts were voiced in a written form in a short period of time.

After the team finished, we stepped back and looked at the big picture of our collective answers. Then we themed the answers. Those themes helped guide the next steps in creating our strategic plan for the next 3 months.

And if there was a question about a comment on paper, I loved asking, “Who wrote….?” This gave space and permission for individual thoughts to be heard as we clarified the themes and next steps.


If this sounds like something you need help with, then here are a few strategic planning questions for you.

Strategic Planning Questions: 

  • What’s working well right now? 
  • What do we need to take with us? 
  • Where do we have momentum? 
  • What potholes do we need to avoid? 
  • What meaningful conversations have we had? 
  • What are opportunities? 
  • What are road blocks? 
  • What do you see on the horizon? 
  • What are the possibilities in the next 3 months? 

If you decide to give this style of strategic planning a try, let me know how it works for you! Give me a shout at the bottom of mattgraybill.com

Planning for a New Year?

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2020 will be a year to remember – but what will you remember and how will you remember it?

I get asked a lot of questions about Year-end or New Year planning. And I’m a firm believer in both: in order to plan ahead you must first look back at where you came from. When you look at this past year, no doubt there are things that you will want to repeat and things you will want to rewrite. You are not alone in wanting to forget many aspects of 2020, but there lessons learned and experiences had that can shape the steps you take in the future.

Here’s what planning for the New Year looked like for me . . .

Below are the questions I posed to our team at South Bend City Church at the close of 2020. before we stepped into planning for 2021. My hope was that these questions would give our team space to “put it all on the table.” This process was both rewarding and difficult at the same time. Even though I came up with these questions, I too had to sit with them for awhile. And what I realized was that there were so many layers to 2020 – much I had forgotten. These questions did exactly what I hoped: they facilitated an open and honest dialogue that was necessary in order for us to move into the new year.

And if I could give you one tip as you dive into these questions: don’t skip the personal learnings they are just as important (if not more) than the learnings you have as a team.

Pre-Team Meeting Work:

Take some time to reflect on 2020 for yourself and for our team. Write down the answers to each of these questions so you will be ready to share and discuss

What did 2020 look like for you?

  • Three accomplishments you are most proud of in 2020.
  • One person, one memory, one practice you are most grateful for in 2020.
  • Learnings: What did you learn about yourself? What inspired you in 2020? What was your hardest moment? In what ways was God revealed to you? 
  • What do you want to repeat and what do you want to rewrite from 2020?

What did 2020 look like for our team?

  • Three accomplishments you are most proud of for SBCC (our team)?
  • One person SBCC had an impact on, one SBCC memory, one practice we did you are most grateful for in 2020.
  • Learnings: what did we learn about ourselves? What inspired us? What was our hardest moment? In what ways was God revealed to us? 
  • What do we want to repeat and what do we want to rewrite? 

Team Meeting Work:

Now talk about your answers to these questions as a team. Set aside at least 2 hours in a comfortable space. It’s helpful if you guide the flow of moving through these questions, but make sure everyone has an opportunity to be heard. This doesn’t mean every person has to answer every question out loud, but it does mean there’s space for everyone to share.

(Check out Part 2 – Strategic Planning: Why are they being so quiet?)

Looking for Ways to Avoid Awkward Conversations?

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Awkward conversations are the worst. I remember the first time I struck up enough courage to call a girl I liked on the phone. I was in 8th grade. I’m pretty sure I said hello and then waited a solid minute for her to say something. And the truth is, sometimes leading a team or connecting with an employee in a 1-on-1 can be JUST as awkward as talking to a girl on the phone, or attending a middle school dance. We are not sure what to say, what to do, or how to respond when we step in front of the room, or when someone approaches us with expectations to be led through a challenging time. Many times, our default is to announce our presence or our agenda and let others speak up if they have something on their mind. But that’s not always helpful to the people we lead.

That’s why I get asked a lot, “How do I make conversations less awkward when leading my team?

Here are a few tips I’ve learned over the years:


Being intentional is key in your relationships in life, especially as you lead people on your team or organization. The same is true at home with your family and your people. When we lead with intentionality, we take away the awkward moments by giving purpose and meaning to the important areas of life. My context for the last 15 years has been leading in the church and I can see how being intentional has been crucial for creating amazing connecting environments and meaningful relationships. Let’s face it, with technology, people are now connected more than ever, but that doesn’t social media is always the ideal connecting environment and it doesn’t mean all of our online relationships are meaningful or have purpose. There are many ways and approaches to being intentional in the way we lead, but I believe one of the best approaches to intentionally is to lead with questions.


Remember that awkward phone call I mentioned with the girl I liked in 8th grade? If I had led with questions, I probably would have saved myself and the girl I was talking to on the phone a lot of awkward pain on the phone that day. My intention was to call and signal that I like her, but I was not intentional with asking her questions. Many leaders have given much thought to how to structure their team or organization, but haven’t given much thought on how to engage with the people who make up the team or organization. Maybe we have a list of people we connect with on a regular basis for meetings, 1-on-1’s, etc., but have we actually asked them any questions?

Questions communicate value in two ways: questions express value to the person whom we are asking the question, and questions show what we value. If we ask a teammate or colleague how they’re doing, they feel noticed and appreciated and we show that we care about them by taking the time to ask the question. Asking questions communicates that someone or something is more important than we are, especially if we listen to their answers! Here are a few other things we communicate when we ask genuine questions:

  • Questions show that you are a learner. You curious about other people and the world around you.
  • Questions help you become a better person. You ask questions because you want to learn and grow so you can make helpful changes as you lead.
  • Questions are universal. It doesn’t matter if you are leading in a non-profit or for profit, a small organization or large organization, questions guide you, help you learn about others, and deepen relationships.
  • Questions create connection. Intentionally leading with questions not only helps us shape community, but it actually creates community.

So, the bottom line to avoiding awkward conversations is to be intentional and ask questions.

If you’re nodding your head in agreement, but you’re not sure how to get started here, then these tips are for you.


Ask your team:

  • Why do we do what we do?
  • On a scale of 1-10, how healthy is our church, our team, and how healthy am I?
  • What is working well?
  • What needs attention?
  • What are the questions we need to be asking?

Ask your leaders:

  • What questions do you have or questions that you getting from others?
  • What are wins you have had recently that are worth celebrating?
  • What tensions are you feeling?
  • In what ways can I help you develop as a leader?
  • How can I support you?
  • How can I pray for you?

Ask yourself:

  • Why am I doing what I am doing?
  • What am I doing that I need to stop doing?
  • In what ways have I seen God at work?
  • What are opportunities that I see in front of me?
  • Who do I need to connect with today?
  • Why am I afraid to ask that question? 

Be Intentional:

  • Schedule consistent meetings with your team, including team days for fun and connection
  • Remember important dates like birthdays and work anniversaries
  • Check in on each member of the team personally
  • Take an interest in their interests
  • Encourage self-care and healthy sabbath rhythms
  • Celebrate their milestones and achievements

I’d love to hear from you, too! How do you avoid awkward conversations with your team?

Who is Matt, and what is this all about?

A bit of my story:

Growing up in Philadelphia, I had dreams of being a professional athlete like Michael Jordan, an archeologist like Indiana Jones, or an architect like Franklin Lloyd Wright. Slowly, reality sank in and new dreams emerged. But not before some awkward family photos, like this:

In high school I thought about becoming a pastor, but then I realized pastors needed to learn Greek and Hebrew (at least in my Presbyterian tradition). Then the realization… I had just gone to summer school for English! There’s no way I was ready to tackle Greek and Hebrew. So I ditched that dream for a new one: becoming a teacher.

My passion for sports and working with people translated into my pursuit of becoming a Health and Physical Education Teacher and a Coach. After 8 years of teaching and coaching in suburban Philly and Central PA, I loved it but still had a passion I couldn’t shake for the local church. By this time, I was also married to my college crush, Beth, and we had two energetic boys. So, after a number of moves (including living on a tiny island in Africa), teaching at 2 high schools, and earning my Masters Degree in Educational Administration (thinking maybe my next move was to be a Principal), I eventually became a Pastor – first in Central PA (LCBC Church), then in Southern CA (Saddleback Church) and now in South Bend, Indiana (South Bend City Church). And just in case you’re wondering, I still haven’t taken Greek and Hebrew. 😉

Over the last couple decades of being a “Gym teacher,” a Coach, a Pastor, a Husband, and a Dad, I have become more aware of who I am and what I have to offer the world around me. I have realized that I like to ask questions, and people like to ask me questions. It is not that I have all the answers, but I’ve had a fair amount of life and leadership experience. And I think the more you ask questions, the more you learn. Asking questions requires a different posture than having all of the answers. It’s the difference between being a student and being the expert. I’m not the expert, but maintaining the posture of student has taught me some really valuable lessons – lessons other people ask me about frequently. And it’s been really fulfilling to share those learnings with the people whom have asked.

What is all this about?

I’m not a blogger. In fact, I’ve resisted starting this blog for a long time. I’ve watched up close and from afar as people promote themselves in really unhealthy ways, and honestly this kept me from wanting to put myself out most times. But a friend recently encouraged me that others miss out on what I have to share because I do not want to come across as a “self-promoting salesman.” #truth

So, this space is all about questions – the questions I frequently get asked as a leader and the questions I’ve been asking as a human. My hope is that communal learning happens when more of us start asking questions and sharing insights in this way. May this be our practice together.

More about Matt:

  • One of the best questions I have ever asked in life was asking Beth to marry me. Beth is an amazing woman, wife, mom, leader. She started her own business as a Conscious Consultant and Collaborative Storyteller which you check out at: bethgraybill.com
  • I get to be Dad to two awesome teenagers: Kallan and Aaron.
  • Our golden retriever, Champ, walks me daily and helps keep me connected to some sacred life rhythms by getting out in nature.
  • South Bend, IN has become our city and our home.
  • I get to help lead a talented crew at South Bend City Church as the Executive Pastor
  • Skills:
    • ORGANIZATIONAL LEADERSHIP: Turning vision into a reality for maximum impact.
    • TEAM BUILDER: Developing and empowering teams towards a common vision and mission.
    • STRATEGIC CONNECTOR: Seeing people connected and organized into the vision.
  • Personality Assessments:
    • Myers-Briggs: ENFJ
    • Strengths: Strategic, Belief, Responsibility, Developer, Woo
    • Enneagram: 8 with 9 wing
    • DISC: D,I

Want to know more about me and what this is all about?

Ask me some questions.