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?

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