I’ve been operating under this company coming into a year now. We’ve had our challenges. There are a lot of grandfathered and inherited issues that can’t be fixed immediately and staff that are not operating efficiently. A lot of set expectations especially due to covid circumstances that shouldn’t exist today.
50-60 days ago, there was a big leadership change. As a result, I was asked to step in temporarily. This was my first time stepping into an independent leadership role for a $32MM operation. It’s weird being here not by choice but because of circumstance. Albeit interim, the partners thought I was a good fit because I have a decent track record. While I appreciate their spoken confidence trusted to lead. In hindsight, they really didn’t have a choice. Of all the lateral leaders, I really was the most qualified but that’s not saying knowing the other candidates. I didn’t feel like I won and while I was “ready” to step up, I deep down didn’t want the job.
My first mandate was to change up the roster and assign my own direct managers so what happened two months ago with this major leadership shift wouldn’t happen again. This was exciting in a sense that I could build my own team from the top. I could bring on younger external people from bigger companies with decent experience in disciplined space rather than the churned managers we currently had. My logic was simple: if they’d done it before, they could help me scale faster.
After two months, this decision taught me some really hard lessons and reminded me that I am no ready to sit in this role for a company that is fairly buttoned up.
Where I am messing up:
I witnessed what it looked like to be a new senior leader managing seasoned managers but I didn’t know what it was like to play the politics. On paper, the reporting lines were clear. In practice, the authority tension was immediate and stressful.
In my first leadership meeting, I asked the new managers to shorten a project timeline by two weeks. Instead of problem-solving, they referenced how “at their last company, these projects always took 12 weeks minimum.” due to very fair buy ins required from other teams. He didn’t frame it as feedback. He framed it as fact. This was very different from how the current staff would interpret. I couldn’t balance the new team’s experience trumping the current team’s urgency. That decision slowed the whole initiative.
I should have set the tone from day one with him. But I doubted myself even though I knew speed was the priority.
Scenario 1:
One of the new managers built a 40-slide deck just to approve a process change, something I would have greenlit with a quick Teams chat thread and a five-minute huddle. I thought I was respecting his style by letting it play out. Instead, it turned into a ton of back-and-forth and delayed the roll-out by two weeks. My other managers were getting pissed off how this was still on our agenda. If I’m honest, the meetings frustrated me as well.
Again, this was on me. I didn’t make clear that while I respected the process, I needed adaptability. By not addressing it early, I let process culture override agility culture.
Scenario 2:
Another blind spot was seeing how different the communication style was between new and current managers. There was definitely a divided being created from the current managers almost staking their claim on things and not losing. Some of us live in Teams and short-form updates. My one current manager expected detailed reports and formal memos. He interpreted one of the new manager’s quick “check-ins” as a lack of seriousness. He interpreted their detailed write-ups as overkill.
During a budget review, the new manager asked for a topline view of a project’s spend. What he got was a 20-page PDF. He says he skimmed it and gave a two-line response. The current manager felt dismissed. His reporting team felt frustrated. No one got what we needed because I hadn’t set the expectation that “high-level summaries” were the standard unless I asked for depth. That mismatch ate away at his team’s trust
My lesson:
The lesson so far is this: hiring new managers isn’t the challenge. Making them fit with existing managers is.
Authority doesn’t come from titles, it comes from clarity.
Respecting current experience doesn’t mean outsourcing direction.
Communication styles have to be made explicit by me, not assumed.
My job as a leader is to define the operating culture, not let the loudest voice set it.
There have also been smaller lessons in other areas but these really stuck because they’re still an ongoing issue I can’t remove right away. The result of all this wasn’t failure in a single project, it was a slow erosion of alignment when it comes to management style. Projects dragged. Meetings turned into debates about “how” instead of moving forward. And I became the referee between managers instead of the leader. I have baked a few strategy plays between my team to see if I can yield different results.
In hindsight, I had failed to do the one thing that mattered: set expectations the way I would have in my previous role and holding the line consistently. I let my inexperience tell myself these guys would set the tone in how my leadership would work. This is going to be a short but painful ride for all of us. I’m confident we will work through this; it just won’t be quick. Right now, the owners are patient and motivating but I think they only feel this way because they don’t have a choice. Luckily we haven’t been financially impacted but we’re definitely skating on the edge. Internally, I’m at the conclusion I’m not ready for the big seat just yet. This is a valuable experience. It wasn’t wasted and for nothing.
The slow and steady entrepreneur
September 30, 2025