Several years ago, during a high-pressure release season, my team missed three deadlines one after the other.
At the time, I did exactly what most managers would do: I added a daily check-in with the team, and started asking for more detailed “status updates” from them. I even started reviewing the project plan every single week, and giving them feedback.
And within a few weeks, things got worse.
When I ran a retrospective with my team at the end of the quarter, it turned out that my team wasn’t “slow”. In fact, they were delayed because they had a dependency on another team that was supposed to deliver an API, and their delivery got delayed.
During the retrospective, when I asked my team lead why he didn’t raise this earlier, he said he thought it would sound like an excuse, so they decided to just keep “trying”.
At that point, I realized that I had mistaken a dependency problem for a discipline problem, two very different problems with very different solutions. All I did was add more meetings, which only made things worse for the team.
I like to compare this with our visits to the doctor or the GP.
Think about the last time you went to a doctor with a headache or some minor pain.
I know there are a bunch of bad doctors out there, but let’s consider what a good doctor would do :)
A good doctor would likely ask you a bunch of questions, such as “how long as it been going?” or “Where does it hurt?” or “On a scale of 1 to 10 how would rate the severity of the pain?” etc.
I know some of these questions can be annoying, and it feels like an interrogration, but if you think about it, they’re doing this for good reason.
A headache is just a symptom, and it could mean one of several things:
Maybe your body is dehydrated
Maybe you’ve been working on a computer too long
Maybe you have an underlying condition that’s much more serious
The symptom is the same (the headache), but the treatment is very different depending on the underlying situation, and the doctor is trying to get to the root cause so they can give you the right treatment.
I find that leadership works the same way, except that most of us like to skip the questions.
Here’s what I’ve noticed and experienced after 20+ years of leading teams: the symptom is what you see or observe around you, but the root cause is what you need to fix. Most leaders I’ve worked with jump straight from the symptom to a solution for the symptom, and skip everything in between.
That’s what I was doing with my team earlier, when I was trying to fix the symptom of delayed releases without trying to understanding the underlying reasons.
I think this is the biggest blind spot in leadership, because it feels like action. Remember that taking action isn’t always productive, especially if it’s aimed in the wrong direction.
So in this post I’m going to discuss the six common leadership problems that I’ve seen in my career, and what you can do to identify the root casue from the symptom.
The Kyoshi beta just wrapped, and here’s what some of the leaders had to say about their experience with Kyoshi: (check out last week’s post for a full introduction to Kyoshi).
I’m an Engineering Director with 13+ years of experience leading engineering teams and building technology platforms. Kyoshi offers a structured, practical approach to learning leadership frameworks and applying them to real-world situations. I particularly love the Practice section, with its role-plays and scenarios that challenge me to think through situations as a leader. What I like most is how Kyoshi turns leadership concepts into practical exercises that anyone can reflect on and apply in their career. -- Aman Agrawal
I’m an Engineering Director leading a small, distributed team. I used Kyoshi to think through a real situation: how to tackle tech debt when the person who built the platform is less available. Instead of handing me an answer, it started by asking a clarifying question, which is what a good coach does. What I like most is that the scenarios feel like real management situations, not textbook cases. -- Sébastien Rufiange
I am a management consultant and a mentorship coach that helps clients make changes to their business or engagement approach to maximise the output and ensure a happy team. I work across industries, and Kyoshi was great at enabling me to make critical decisions about both my commercial terms and also my engagement process using the Leadership OS. I liked the pragmatism that Kyoshi gave me and think that this would be beneficial for many in the future. -- Kiran Sudhakar
🔥 The waitlist closes soon (on Oct 20) - join now to be among the first to get Founding Member access.
1. “My team agrees in meetings, but then nothing happens”
You are an engineering manager and run a project meeting with your team. In the meeting, you share the new on-call rotation plan starting next week, and what each individual team member would need to do as part of the on-call duties.
In the meeting, nobody says a word and you think everyone is okay and aligned with the plan. However, two weeks later after the on-call kicks in, you notice that some of the team members aren’t actually able to handle their rotations.
Your first instinct is to send a follow-up email with clearer action items - maybe they just forgot or aren’t clear about what’s expected.
But then you realize that it may or may not help, depending on why the team didn’t respond to the on-call:
The Abilene Paradox. Perhaps the team members privately disagreed with the plan, but went along because they thought everyone else was on board.
Unclear ownership. Perhaps everyone assumed that someone else would take the first step.
Low trust. Perhaps your team doesn’t feel safe saying no to you, so they say yes and then just don’t act.
👉🏻 Key takeaway: Just because you didn’t hear any disagreement in a meeting, it doesn’t mean that everyone is committed to the plan.
2. “My top performer has gone quiet”
Chris, a Principal Engineer and your top performer, used to be the first to raise his hand when it came to hard problems. However, you’re noticing that lately he is keeping his head down - just focusing on his work, delivering on time, but he’s very quiet in meetings.
You decide that he is probably bored and needs a new challenge, so you meet him in a 1:1 and offer him a stretch project.
He doesn’t seem super excited, but to your relief he accepts it. But a month later, he resigns.
Here’s what could have been going on:
Burnout. Chris was still delivering, but his energy was low. Perhaps he was just burned out due to long hours and no breaks.
Boredom. Chris had outgrown the role, and the work because too easy for him, so he stopped asking questions since he already knew the answers.
Something feels unfair. Maybe Chris just didn’t feel seen or recognized - perhaps he was expecting a promotion that went to someone else in the team.
Something outside work. Maybe Chris was just dealing with something in his personal life - like a difficult relationship or a personal loss.
Your stretch project assumed he was bored, but that may not have been the root cause.
👉🏻 Key takeaway: Disengagement almost always has a trigger, so find it before you offer a fix.
3. “Deadlines keep slipping”
Your team has missed its last four release dates, and your Director is looking for an update. Your first instinct is to push your team for better estimates and add some buffer to add some wiggle room.
But the slips could come from:
The Planning Fallacy. Have you noticed how we underestimate how long work takes, even when we’ve been wrong before? Yes, it’s a real trap, and I’ve seen leaders fall for it over and over again.
Too many priorities. Your team’s attention is split across five “priorities”, so they’re naturally not able to focus on one thing at a time.
Hidden dependencies. Your team is waiting on another team, just like the example I shared at the beginning.
Scope creep. The team is chasing a moving target, as new scope is being added constantly. What you had planned for 6 months ago is no longer the current scope.
Adding buffer can hide a delay in a release, but it doesn’t actually address the core issue.
👉🏻 Key takeaway: Before you fix the estimates, find out where the time actually went.
4. “Nobody speaks up in meetings”
When you end your team meetings and ask “any thoughts”, you mostly get silence.
And you conclude that you need to build psychological safety, so you call an trainer to run a workshop.
But the behavior could be coming from multiple reasons:
Low psychological safety. If indeed your team hasn’t seen you encourage openly speaking out in meetings, they may be feeling unsafe.
You’re anchoring them. Many managers do this, and you may be doing this too - you share your view first, and then ask others. What this does is anchor the conversation around your views.
There’s nothing to decide. Sometimes, the meeting is just a status update, and it may “feel” like a discussion, but it’s not.
👉🏻 Key takeaway: Silence doesn’t always mean that people feel fearful of speaking up. Sometimes the problem is the room, not the people.
5. “My team escalates everything to me”
You realize that you are constantly bombarded with decisions your team should be making: which vendor to pick, which bug to fix first, whether to push a release, etc. etc.
And what do you do? You give your team a speech in the next team meeting on how to “be more empowered.”
In reality, those escalations could be coming from:
Unclear decision rights. Your team doesn’t know what they’re allowed to decide, and what they’re not.
Learned helplessness. Maybe you have overruled them before, so they don’t feel empowered to make those calls.
A skill gap. Perhaps they genuinely don’t have the skills or experience to make the decision.
👉🏻 Key takeaway: You can’t force empowerment. Your team learns it from what happens after they decide.
6. “Two of my senior people can’t work together”
Mei and Jordan are two of your best tech leads, and they can’t get through a design review without an (unnecessary) argument. You assume that it’s just a personality clash, and call them both into a meeting to “clean up the air”.
Hmm…
In the meeting, they’re both police and friendly, but the following week they’re fighting again.
Here’s what might be happening:
A personality clash. Yes, this could be real, and could be the reason why they’re clashing again and again.
Conflicting goals. Maybe Mei is being measured on the speed of the system, while Jordan is being measured on how realiable the system is. They’re both working from different goals, which leads to the conflict.
Blurry ownership. Maybe both Mei and Jordan think that they own the system, when neither of them does. They’re not clear about what part of it they own.
👉🏻 Key takeaway: If you change the people and the conflict would still exist, then it’s a system problem, not a people problem.
How to diagnose before you prescribe
I admit that as a leader you won’t always have a neat list of causes in front of you. But you can run any situation through three questions before you reach for a fix:
What changed? Symptoms usually start showing up at a certain point, and it’s useful to know when.
Is it one person or everyone? If it’s one person your team, it could be the person. But if everyone is facing it, you need to look at the system.
Where else does this show up? Real root causes rarely stay in one place. If Mei and Jordan are fighting, check whether other cross-team pairs are too.
When I look back at those three missed deadlines that I was talking about at the beginning, the fix wasn’t more check-ins. It was a 30-minute conversation with the other team’s manager.
I had literally spent six weeks treating the wrong problem.
👉🏻 The fix is rarely the hard part. Finding the right problem is.
P.S. Diagnosing before prescribing is the core of how Kyoshi works. When you bring it a situation you’re facing this week, it asks the questions a good coach would ask before it hands you a framework.
The waitlist closes Tuesday, Oct 20, when waitlist members get access.
Check out last week’s post for a full introduction to Kyoshi:
