Debugging Management

A recurring theme I’ve seen lately is executives being unhappy with the performance of their management teams. Unsurprisingly, with most startups slamming the brakes on hypergrowth, leaders have now become more aware of gaps in their organization’s foundation. Having forgotten that management is a profession, now you’re facing a rude awakening. Here are the seven most frequent issues and suggestions for debugging them.

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Not Autonomous Enough

As an executive, one of the benefits of having managers under you is the ability to focus on more strategic things and have them take care of tactical issues. You might be eager for them to charge forward without you. However, they’re like shy toddlers, holding on to your pants and hesitating to go forward on their own.

Luckily, this is an easy matter to tackle. Since they’re coming to you for help, all you have to do is stop being an enabler. For example, instead of answering their questions, ask for their instincts first. Rather than being approachable all the time, ask them to refrain from contacting you if things aren’t urgent. Also, consider the typical requests you’re getting and compile guidelines.


This is when you see your managers not focusing on what really matters. Perhaps they’re introducing work that doesn’t matter, demanding more tech debt work be tackled in a critical sprint, or prioritizing the wrong thing.

Many executives don’t fully comprehend the context gap between themselves and those under them. They sometimes forget how much more focused they are on things like quarterly goals and the bigger strategy. You can start by simply asking them at your next management meeting (you have those, right?) what they believe are the current priorities. You’d be surprised how a team of N managers tends to have N+1 different answers. That might indicate that you’re not sharing the strategy clearly enough or that they lack product mastery to prioritize correctly.

Then, implement a (light) process to ensure circling back to the real priorities. When goals aren’t announced at the beginning of the quarter and resurface a week before its end but are constantly referred to, it becomes considerably harder to wander off.

Not Speaking Up

As things scale, you can no longer keep track of everything going on at the tactical level, and that’s fine. This is what delegation is all about. Things become problematic when you notice that things aren’t being brought to your attention on time (or at all). Perhaps important deadlines were missed without someone raising a flag earlier. Or your managers had misgivings about a particular decision yet only spoke up after the fact. “I knew it” is rarely helpful if it wasn’t preceded by, “I think that…”

There’s no easy way to solve this, and sometimes it stems from a lack of psychological safety or a culture that doesn’t encourage candor and healthy chutzpah. A diagnostic to help you spot the problem and generate effective chutzpah is available here.

Too Hands-On

This is a phrase I hear repeatedly, but it can mean entirely different things. Sometimes, we mean that the managers are too involved in day-to-day in a way that prevents them from operating at a higher altitude. For example, the team is performing well, but the managers aren’t providing coaching and mentoring to improve things even more or help the team prepare for the challenges ahead. A different case is when “hands-on” is a nice way of saying they’re essentially micro-managing the team. Of course, these can also be two sides of the same coin, part of the same negative feedback cycle.

Perhaps you’ve noticed some of this resonates with the first issue mentioned here. Unsurprisingly, handling managers who aren’t autonomous enough and ICs who aren’t is similar. Practically speaking, you should be putting your coaching attention on helping managers “rise up.” How does one delegate better? Do they need to coach their own people, build trust, put in processes to reduce errors and allow more safety to operate? Whatever it is, get on it.

You Don’t Trust Them

Trust is often at the crux of micro-managing and avoiding coaching toward autonomy. If you simply don’t trust your people to do the right thing on their own, who can blame you for being involved, right? And while I agree you should keep your finger on the pulse, especially in these cases, that’s not handling the root cause of the problem. One should not hold a management position without trust; that’s an oxymoron.

First, if this happens across the board, as I’ve seen in some companies where the executives don’t fully trust anyone in their middle management, you must consider the common factor—yourself. Are you hiring the wrong people? Are you failing to coach them? Perhaps you have trust issues? It could be that you’d benefit significantly from intense coaching yourself to move past this obstacle.

Second, in the case that the issue is limited to specific individuals, take action. When I wrote about coaching for (your) sanity, I covered the different types of work you can perform to build trust even when the stakes are high and get your people where you need them to be. If, after a (relatively short) period, you don’t see enough progress, something is not correct.

Too Techie

Since the vast majority of engineering managers have a background in… engineering, they sometimes have issues collaborating with others. It could be that when they’re asked to communicate things up to the business stakeholders they find it hard to convey the right message or use too much jargon. Or, they might not proficiently collaborate with their peers in the company and are too reliant on your involvement to do the speaking for them.

I see this more often when working with engineering managers who don’t have experience operating in cross-functional organizations. Due to that, they’re used to communicating with peers through “APIs” such as Jira tickets and relying on management to do the translation. The product mastery mentioned earlier to help with alignment, and focus is also greatly useful to enable better communication. Understanding the business and its goals means they will find it easier to speak about things, not in their technical aspects, but consider the why behind them and explain things like tradeoffs better.

Poor Risk Management

And lastly (for this installment), you might be seeing issues with how your managers weigh different options. They might be miscalculating how big a decision really is and making it without due process, or they might be on the opposite end where they waffle too much, even the more trivial issues. Risk management is one of the core skills of leadership that might be at the root of several of the previous problems covered, even though I find that executives rarely pinpoint it clearly.

There are a few ways to tackle this, but the method I’ve found simplest and most effective is to ask them to write things down. When they’re waffling a decision, write down the different possibilities, how the risk can be mitigated, contingency actions, etc. Then, given what they wrote, they should write their suggestion. Now, instead of coming to you with problems, they will have to do so after taking ten minutes to write their reasoning. This will allow you to debug their thinking in case they’re missing things and also make it clear when their instincts have improved.