Debugging Leadership Growth

If you look at the leaders under you in your organization and are unsatisfied, remember that you are what they all have in common. I’m not saying it to chastise you but to realize that you have more agency and influence than you might recognize. For example, when it feels like people don’t have broad shoulders, you can help them get there faster than most would expect.

The real issue is that the steps needed are… unsexy. It’s common sense and discipline, nothing fancy. Leadership is a quotidian effort, not something you can “do” in one meeting. If you’re open to hearing some common sense, here are common complaints, questions I ask to debug them, and suggested approaches. Imagine that the questions are my “debug prints.”

”People don’t take the initiative”: Did they ever? If so, and they stopped, what happened when they tried it? Were they chastised for mistakes, or did you swoop in to micromanage them? If they never were more proactive, did you provide that feedback and make room for them to do so? Create the environment to enable this. Therefore, speak about what it means, give examples, explain how you’d handle conflict and mistakes, and mentor them as they go about doing it.

”I can’t trust them enough”: Is this across the organization or specific individuals? The former might indicate difficulty in letting go and coaching on your end. If you can trust some, make the bright spots shine: try and mimic what they do or replace people who simply can’t do that. That way, you’ll raise the bar. Otherwise, when you can’t trust anyone, it usually means you’re the one keeping all the plates spinning. In my experience, that creates a negative cycle where people become more dependent on you, you trust them less, intervene more, and thus, they become even more dependent, etc.

“We (senior leadership) are overwhelmed”: Are you involved in many things? How many of those are genuine senior leadership stuff? If it’s justified, scale out to more people (i.e., increase the executive team); otherwise, make delegation a success metric for executives. Reduce drive-by questions to a minimum and be available in defined bursts for anything not urgent. You’d be surprised how much it helps identify patterns and reduce noise.

”Not enough collaboration across orgs”: Is senior leadership collaborative enough among itself? If not, you can bet everyone’s mirroring you. Other times, it might be that executives are doing most of the peer communication to an extent that doesn’t allow for enough “healthy friction.” Set up joint projects, exert effort in effective matrix management, make people “3D” (e.g., have different departments share their wins and challenges so others get a real understanding of their work as opposed to some superficial image).

”Leaders are too tactical”: Do you take the time to speak at a higher level regularly? Do you even have a strategy? For each person who is strategic by default, I’d wager there are 50 who tend to be too tactical. Without working on strategy together and making time for thinking, you’ll get a barrage of “strategies” and no unified effort (e.g., you don’t need a “tech strategy”). Make the time and create a strategy (for help reach out). Share it and measure the organization by it. Simple yet hard.