From Manager to Executive - Unexpected lessons learned
The transition from manager to executive can be extremely jarring with little support. Get a leg up by understanding some of the executive realities you will encounter.
Everyone knows how jarring a transition it is when moving from an individual contributor to a manager. Everything changes: the skillsets, the responsibilities, the scope, the tradeoffs. There’s been plenty written about supporting ICs through that.
Significantly less is available on the just-as-jarring transition from middle-management to executive. The stakes are higher, and the scope and responsibilities wider, and the possible impact exponentially larger.
Having been in the executive-level leadership seats multiple times now, I’ve learned a lot of lessons. I hope these lessons help former managers who may be new to the executive role, or managers who are thinking about entering the executive role.
What have I learned?
People will be unforgiving.
There’s little margin for error.
You shouldn’t solve all the problems you see.
The best solution might harm your team.
Every decision you make will have someone who hates it.
Executive discussions can be messy, intense, and unfiltered.
You have to accept blame for things you didn’t want to do.
You have to accept blame for things you had no control over.
People will be unforgiving.
As a leader, your actions and reactions create the environment your organization operates in. That shapes how they behave and think, whether they feel safe to act or not, and whether they are ultimately effective or ineffective.
You do your best to create an environment where people are nurtured, free to make mistakes while still being held accountable, and free to bring their best selves to work. You might call it creating “psychological safety” or allowing people to be their “authentic self”, and it’s your responsibility as a leader to make space for your team to do their best work.
Ironically, that benefit will not extend to you as an executive.
This surprises many middle managers who rise up the ranks under the protective environment their leader has developed, only to find that the protection stops at some point between Director and VP.
The truth is that the people in an organization don’t want their executives to be their authentic selves, with warts and flaws, even if they say they do.
When was the last time you heard an executive flaw spoken about as “they’re just being authentic?” If anything, any issue is highlighted as a sign of their unsuitability to leadership or indicators of incompetency. People derive judgements, not understanding, from flaws, mistakes, and foibles.
Most people want flawless leaders while simultaneously not wanting to be held to that standard themselves. People don’t want leaders who have a quick temper, or lose their cool in crises, or are unavailable because they are busy, or don’t know their work extremely deeply, or are late to meetings.
As an executive, when you fail to live up to the standard of perfection (which you will, often), you will hear complaints and criticisms from many different directions. In the rare situations you do manage to be perfect for a season, people will then hold you to account for being too perfect - intimidatingly unemulatable.
There’s no winning. There’s no perfect. You have to be willing to accept that, while still striving to be the best you can possibly be.
Although difficult, you have to not let this reality change how you view other people. Continue creating safe environments where people can grow and improve and bring their best selves to work. While you may not be covered by the umbrella, it doesn’t mean you can’t continue holding it for your team.
Once, after a round of lay-offs, I had to prioritize the survival of the company and push the team to release a set of capabilities that would stabilize the company and help it live to fight another day.
We released it successfully after several weekends, and while it was positive and impactful, the team was spent. I told the team to rest up, while simultaneously pushing back heavily against other leadership’s demands to do even more. Both were important: to give space to the team to rest but to also ensure the company continued operating.
To support the team, I personally worked nights and weekends to give the team a normal schedule for a few weeks. This was successful - the team was able to work standard hours, and we still managed to deliver additional key initiatives during a tough time for the company.
In my review that quarter, the team complained heavily about being forced to work after-hours to save the company. They also complained about my own after-hours work, noting that they felt it set an unrealistic expectation.
There’s very little margin for error.
If you’re working in a healthy organization as a manager, you’re not going to end your career over a mistake. They’re treated as learning opportunities that are necessary part of the improvement and growth that people experience. Sure, you might have to discuss the details with someone, or implement follow-ups or action-items to improve, but that’s not even a slap on the wrist - that’s just healthy retrospection and improvement.
Managers are often in for a shock when they become executives and realize they no longer get that benefit of doubt that has enabled them to learn and grow. There’s very little margin for error.
In some cases, mistakes are a “one-strike, you’re out” situation.
Why?
At the executive level, the impacts of mistakes are magnified - consistent excellence is the expectation.
This standard is correctly higher for executives. When you make a mistake as an executive, it has the potential to lose millions of dollars or cause an organization to collapse.
You need people in those seats consistently firing on all cylinders.
Minor things can set off a chain reaction that leads to a failing in the role. I’ve seen dozens of such moments across the companies I’ve worked with. First-time executives may expect forgiveness only to encounter a job-ending landmine.
Even in my own career, I’ve lost out on promotions or had teams pulled because of a mis-step I’ve made, and even in some occasions something one of my reports did against my explicit instruction.
Some of the reasons I’ve personally been penalized as a leader:
One of my reports wrote a passive-aggressive message to their team
One of my reports didn’t manage a new report on their team effectively
Publicly favored a recommendation by the COO over the CTO.
I made a joke about sunsetting a product that was close to the C-level’s heart
I spoke up against an unnecessary multi-million dollar expenditure
Penalties at the executive level aren’t a simple talking to. Instead, they’re significantly more impactful: a harm to the company, a loss in team, a rejection of a promotion, or even an eventual replacement.
I’ve seen other leaders penalized over things like:
Putting in the wrong number on a presentation
Having a bad day and momentarily losing their temper in a single meeting
Not matching the communicativeness of other leaders
Disagreeing with someone in a public forum about a key issue
Being surprised at news about one of their projects that they should have known
Having a message’s tone misinterpreted by a key stakeholder, leading to conflict
Having a highly visible but fairly minor project delayed
Making the wrong hire
Taking too long to hire
Accidentally forgetting to do a task amongst the hundreds on their plate
Their boss leaving
You typically don’t get a warning when people lose confidence in your leadership. It just happens.
In the hot-seat, first-time executives can get paranoid and more controlling, unintentionally inflicting further and further harm on their organizations. They eventually create a self-fulfilling prophecy where their desire to be perfect causes them to fail. It’s an unhealthy mindset that takes a huge perspective shift to combat.
The best way to deal with it? Take these hits on the chin and adapt for the best of the organization. Help support your organization, your team, and your reports. Accept that things will happen, and you’ll do your best for as long as you can, and you’ll leave the organization better than you found it.
That’s really all you can do.
You shouldn’t solve all the problems you see.
When you’re an executive, every single problem in the organization is visible to you across the entire organization. Personnel conflicts, failing processes, strategic mis-steps. Everything.
These problems are also rarely within your direct ability to solve. Some problems are intentionally left alone to help further another organizational goal. Others are problems, but they are a low priority relative to other problems the organization is solving.
Even trying to solve a problem can cause a whole host of issues that lead to significant waste and even more issues, especially if it crosses organizational boundaries. No executive likes it when someone else solves a problem in their organization that they were already handling, causing other unintended issues as a result.
Executives have to have the ability to view a problem, and accept that:
It isn’t time to solve that problem
Someone else is already solving that problem, and you should not be involved in any way
The problem may not be one we want to solve
This, as it turns out, is extremely difficult for people who come up from management, where the whole role is about solving all of the problems within their view. As a result, they start to get overwhelmed at the amount of problems, or over-step in their desire to help, causing more issues than they solved.
The best solution might harm your team.
When a first-time executive solves a problem, they often apply manager-level thinking, optimizing for their function and near-term time horizon. This usually solves the immediate problem but negatively influences a farther-term outcome.
It’s often the cause of feedback of “not thinking strategically”.
Imagine a first-time executive who sees complaints from developers being frustrated with deployments, and fights to build a new team to handle those operations. They successfully argue for a million dollar budget and build the team. That leader might view that as a win in the short-term: they got the budget and they were able to hire and solve an immediate developer pain point. But at what cost? What else could the money have been used for in the organization? What happens if that budget was taken away from a new marketing initiative, or a struggling sales organization?
What about the mid-term? What if that new team takes on operations, causing disruptions to day-to-day activities as they onboard and make mistakes. Bottlenecks start to form. Batch size increase. Change failures and incidents occur more frequently.
What about the long-term? What happens when the rest of the organization loses their knowledge of how to set up operations, and as a result the organization’s ability to safely deliver changes rapidly to production decreases. Gate-keeping behaviors start to form, and hand-off cultures start to be developed between development and operations. Blame culture starts to develop when things go wrong.
Eventually, what seemed to be a huge win initially turns out to be a massive liability.
Why is this so different?
When you’re a manager, your problem space is your teams. Problems are immediately within your area of responsibility to solve. You see occasional challenges with your peer teams, but otherwise you don’t have to deal with fixing those problems - those teams’ managers can handle them, and other things can be escalated.
The problems in the managerial space are mostly tractable - they all have some sort of solution that you can discover and deliver that provides relatively immediate feedback on whether the problem has been solved or not. Trade-offs inform which solution is “better”, and these are typically articulated by the executive leadership.
When you’re an executive, problems have complex inter-relationships involving differing trade-offs, information asymmetry, and a web of complexities inherent in the organization.
Most problems you solve will not have clear or easy answers. Each one will have long lists of pros and cons with large, lasting impacts for getting it wrong. There’s typically no “right” decision at all. Just a bunch of decisions that’ll have positive impacts to some and negative impacts to others. Some are intractable - things that will never be solved, only mitigated.
Many solutions have different outcomes depending on whether you look at it across months, quarters, or years - a roller coaster of ups and downs far disconnected from the original decision. Optimizing a solution for the wrong time horizon may result in many downs later in the track.
It makes sense - if the decisions were easy or straightforward, anyone could make them and the executive wouldn’t be needed to make that decision. You’re only involved in that decision because of the implication and potential effects. Someone has to take ownership for that decision, and that’s the executive.
When you’re an executive, you have to think across multiple time horizons and scopes. Sometimes, you do what’s worst for your team or even yourself in the short-term to mid-term to ensure you do what’s best for your organization in the long-term.
Every decision you make will have someone who hates it.
Because of the scope of the problems you are trying to solve, and the pros and cons of them all, it means that every decision an executive makes will have detractors somewhere in the organization.
Managers are used to an environment where they can reliably keep most people happy and satisfied through their actions. They operate at a layer where they can build direct relationships with their immediate teams, and effective decisions are generally mostly aligned with team happiness. Good managers keep their teams morale high and often find solutions that optimize for their team’s happiness and the team’s effectiveness.
When managers become executives, the amount of people who might be unhappy at something they do can be shocking. Most decisions do not have an “everyone is happy” solution.
I have a rule of thumb that I follow with any decision I make:
30% of the org will be unhappy, and tell you
30% of the org will be happy, and won’t tell you
30% won’t care either way
10% will dislike it enough to complain to your boss
This means every decision, no matter the outcome, will be second-guessed by someone in the organization who has a less nuanced perspective. People will talk about how you made the wrong call, or should have done something completely different. They’ll bring up their issues to you, their peers, others in the organization, and yes - your boss as well.
As an executive, you (and your boss) will mostly be hearing negative feedback about what you do. It’s a tough transition for managers where in the past doing something successfully meant everyone in their sphere was happy. It’s hard for people who are used to calibrating via positive feedback.
If you have a good boss who listens to the negative feedback they get, nods their head, and doesn’t use it negatively against you - great: you’re in a perfect situation where you have your boss as a partner. They understand the realities of being an executive and have your back.
If you have a boss that takes any piece of negative feedback they get and immediately penalizes you and uses it against you: not so great, because you’re naturally in a role where everything you do will have some negative feedback around it.
The best way for managers-turned-executive to deal with this is to not stress about trying to make everyone happy. Instead, their goal should be to make the organization more effective. Calibration should be done on the desired outcomes and time horizon, not whether people are happy about it or not.
I once organized a change that involved spreading subject-matter-experts across each of the teams to support increasing their access to domain knowledge.
We were previously following a center-of-excellence model that simply was not working: bottlenecks were forming, there was a lack of incorporation of their expertise, and there was a lack of awareness of ongoing work.
Once I announced the change, there were significant complaints about it from various parts of the organization, some of who went above my head to the president to complain. They wrote pages and pages of how this was a terrible idea and how I was an ineffective leader and also demanded a meeting.
The president, luckily, was not a reactive leader. He met with me and I explained the reasoning, and he understood and disregarded all the negative feedback.
Three months later, the change had been extremely positive. As a result of having direct, dedicated access to experts, tams made significantly better decisions that were effectively de-conflicted and were no longer bottle-necked on a central committee.
Executive discussions can be messy, intense, and unfiltered.
Managers might envision an executive team as some sort of organized secretive group of wise experts sitting in a dark room with robes like Illuminati. They carefully and cunningly discuss problems and cast a secret vote on a solution that then gets imparted to the masses.
In my experience, executive discussions are a lot messier. Truly difficult decisions tend to be more like an all-out brawl where ideas quickly get presented, shot down, swiss-cheesed, and built back up. It’s a raw mess that can get quite intense. It’s often the opposite of most team-level manager-led discussions that are usually organized and more harmonious.
People who get a glimpse into how the sausage is made may come away with the sense that the executive team is chaos, or doesn’t know what they are doing.
That’s not an accurate perception.
When you are dealing with potentially intractable problems across a dozen different functions, the ability to rapidly hone in and really debate is key to arriving at a decision that weighs the tradeoffs in the manner best for the organization as a whole.
Managers may be used to softer, more harmonious approaches to discuss and debate ideas with their team, but these only work when the team is composed of mostly aligned individuals that are part of their function or peer function. Their first contact with an executive discussion might be extremely jarring: punches are not pulled, people say what they need to say, and ideas are shot down just as fast as they are brought up.
Keep reading with a 7-day free trial
Subscribe to Joseph Gefroh to keep reading this post and get 7 days of free access to the full post archives.