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Leveling With Your CEO Effectively

Managing Up
Managing Expectations
Convincing

1 June, 2021

Stefan Khan-Kernahan
Stefan Khan-Kernahan

Director of Engineering at Beanworks

Stefan Khan-Kernahan, Senior Engineering Manager at Beanworks, harnesses the power of negotiation when bargaining for the time and resources necessary to meet the objectives of tomorrow, without losing sight of the needs of the present.

Problem

I joined my current company right before the Series A round of funding. Due to funding constraints, the team was quite small, and many people wore multiple hats, doing whatever was needed to be done as quickly as possible. When working at this level, most of the financing will be personal, so a high degree of trust is required when convincing your boss to go one way or another.

In this type of scenario, knowing how to manage up concerns as they present themselves is so important. Learning how best to explain technical issues to our CEO, an accountant by trade, was a long journey for me and my team. We needed to learn how to communicate the way that we were analyzing problems and prioritizing our tasks.

To them, at times, the amount of effort and attention given to certain business-related matters was not in alignment with what they believed our needs were from a technical standpoint. We were expending effort minimally in a few areas, doing what needed to be done to address our tickets and devoting more of our time elsewhere, in longer-term investments.

Our whole team got together in order to come to a solution. Some of the things we wanted to do would not see results for upwards of two years but would really help the development team, and we needed time and the hands to accomplish these goals.

Actions taken

The way around it involved speaking on their terms as a financially-minded individual.

Our analogy: they have five credit cards. Would they rather pay the minimum balance on all of them monthly, trying to manage their spending so that they all pay off at the same time? Or would they rather double down on the balance of one card, and then the next, and the next, until they have all been paid off in full?

They said that they would not put in the minimum balance across all of the cards, because it would be a waste of time and money; they would focus on one at a time in order to avoid all of the accrued interest. We found that a big part of whether you win or lose a conversation concerning a long-term decision involves understanding that the person you’re managing up to really needs to be able to defend the decision made at the end of the day. Your CEO has a boss; they’re the founder, but they have a board that they answer to. How do they prepare themselves to go to their board meetings and explain why they’re making the decisions being made?

This is especially relevant when you are trying to persuade your CEO to move in a direction that will not see any tangible results immediately. We wanted to show them that we intended to be with the company long-term and that these investments would lead them to the results they want in the long term. The cost, to them, appeared high. We walked them through scenarios and showed them how much easier things would be if we did them in a certain way.

After getting the initial buy-in, we kept them in the loop by showing them visual ways that our propositions were improving the systems that we were working on. At times, my back-end-focused team was often left waiting as the front-end team did their part, but the trade-off was worth it in the long run.

Lessons learned

  • In development, you can’t change everything in one go. To do so is to change the tires of your car while the car is still going. Keeping your CEO on the same page with you as everything unfolds will allow them to remain engaged with the process until the desired outcome has been achieved and is apparent to them in a way that they can understand. Suddenly, they see the system is able to provide a deeply technical function. This is difficult for people who are not technically-minded to see until the final result.
  • After you are able to prove these abstract plans to them, you earn their trust. This trust feeds into the next decision. If we don’t do this now, we’re just keeping things a certain way. If we take a pause on this bigger thing, we may be able to put ourselves in a more favorable position in the future.
  • Managing up is not simply introducing a new idea for a feature. It involves offering things that will benefit the company as a whole. These things will be very specific to your CEO and the industry that your company is a part of. Different companies will have different reasons why they will and why they won’t do something. You need to learn how to speak to your CEO specifically.

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