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?