Set Realistic Expectations with Upper Management

Problem

I recently acquired a team. Things looked seamless on the paper: I had a set of well-defined OKRs and the clear direction the team was to follow. But as soon as I started to have one-on-ones with my team members, I realized that we had a skill set gap. As it seemed, upper management had somewhat different expectations on what the team was capable of doing. Becoming more familiar with the team’s competencies, I had to explain where the gaps were and how we could close them. Essentially, we needed different people with different skill sets in order to achieve what upper management wanted.

Actions taken

First off, I made sure to talk to each of my team members and map out their skill sets. After collecting all the information, I was able to list down the team’s competencies and expertise. I compared those with results stipulated in our OKRs to understand better what we could deliver and what we couldn’t.

I made sure to communicate with my manager the actual situation on the ground as soon as I had some solid insights: this was where we were, and those are the expectations upper management had. The reason behind this discrepancy was that we didn’t hire for current but past goals. This is a common scenario in scaling organizations: goals change lightspeed fast, and one should supplement the team with the new skill set on the fly. We managed to meet the initial expectations and build some of the tools but to move further on, we needed different skill sets.

It took me a couple of sessions with upper management to make my case. I started with a rather rudimentary explanation of where the gap was. Based on their questions, I started to collect data points that fully equipped myself to answer their questions. We also did some demos showcasing what we built and using sprint boards that made more visually appealing the work our team was pulling at that moment. For us to do more, we had to overcome an evident skillset deficiency.

My presentations were met with understanding and acceptance. Once upper management was able to grasp the scope and causes of the discrepancy between the existing and needed skill sets, they were willing to greenlight us to take action. That meant hiring some new people. We worked with the recruitment team to develop job descriptions for roles we were trying to fill and eventually managed to supplement the team with the right hires.

Lessons learned

• The needs of a growing startup can change overnight. People we hired six months ago are not people who can tackle the challenges of today. When I walked into the team, with well-defined OKRs, everything felt doable. But after observing and interacting with the team, I realized I jumped to a conclusion too quickly.
• I relied too much on my past experience: what works at company A doesn’t have to work at company B. At first, I was unconsciously applying that approach until I realized that it was inappropriate in the given situation. The more appropriate approach would be to better understand where my team comes from and what problems they are facing along with the goals we plan to achieve.