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17 June 2020
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Sink or swim: Tips for retaining A-players in the early stages of your startup

You are examining exit interview notes of your so-called “A-player” who resigned a week ago. In every line you read, the pupil of your eye is getting bigger and bigger. Is this the person that you hired?

How come they turned someone blaming, complaining and seeing the world in a different light? Everything was different during the interview and after… How did it turn out this way in 4 months?

Attracting A-players is tough for sure, but the hardest part is to retain them. And losing them is hurting more than rejecting them at the beginning. In this article, I will elaborate on pitfalls that we need to know when we hire an ‘A-player’ and suggestions to avoid these pitfalls.

Before going further, let me share a rough definition of A-player for startups:

Although every business requires different skill sets, my definition for A-players in startups is self-initiating, result-oriented, strategic-minded and enthusiastic people that help you to carry the organization to the further steps.

During my startup journey, I have experienced moments that I hired the person with an expectation of having an A-player and ended up losing them in the end. However, I had good stories as well. But the key discovery after all those experiences is the following:

A-players can perform their true potential only if we are able to show A-Level leadership and enable them within the organization.

Let’s see what are the pitfalls that can cloud our leadership vision and the ways we can avoid them.

Undermining the effect of initial learning

Our intuition leads us to expect potential A-players to perform as we could perform the very same task. I doubt that it is realistic. You are the one with the full organizational history of failures and successes. You know the trials and errors – especially errors – that your organization experienced so far. You know the texture of your organization if some solutions are applicable or not.

On the other hand, your A-players have not walked through any of these paths yet. One good example comes from our recruitment process. We assigned one of our fresh blood to the task that she used to have very relevant experience. However, her initial draft was full of ideas that make a lot of sense but also proven to be ineffective before for our organization such as targeting ex-employees of marketing cloud companies, etc.

One crucial advantage of being a founder is to have this historical knowledge. This set of learning generates the necessary insight to make the right calls. But it is not easy to transfer this learning since there is no time for keeping a diary.

At the end of the day, your A-player might be talented probably more than you are but this lack of historical knowledge may degrade her/his capabilities in your perception. So, is it really reasonable to expect them to perform the initial tasks at such a level? Of course not, but we expect this anyway.

In those moments, remember that you had also been so surprised about the unique business learning for the first time that you acknowledged. However, you immediately internalized it and accepted it as must-know.

Consider again now. Is it right to expect every smart person especially your A-players to know those learnings instinctively? If yes, then don’t get surprised once you lose your A-player. If no, then what shall we do?

Use the power of feed-forward

There is no button you can push and transfer all know-how. Even if there is, it would probably require so much time for the receiver to digest this knowledge in order to put it into action.

Feedback is, of course, an important mechanism to improve their practice but given in the end. However, if we wait for our A-players to make a mistake to share learnings and expectations, we set them up for failure rather than enabling them for success. Then, what can we do instead?

Answer these three questions to your potential A-player & encourage them to get a full brief while giving a task to them:

Ignoring the importance of playground

One of the other common bias is to think that your folks will engage with other people in the same way that they do with you.

As Carl Jung concludes, the interaction between two people happens in a similar way that the chemical substances react to each other. Every relationship shows unique patterns and the end communication depends on the interaction of different personality types of those people.

Considering what Carl Jung explains, your relationship with your folks as a founder will be totally unreplicable for sure. If you miss this reality and don’t empower your A player, she will be guideless when she navigates within the organization. Remember, as she is in a lack of key business learning, she is also in lack of playground you have.

At the same time, this situation is a complete roulette.

If you encourage them too early, it may also backfire since it can put pressure on key people within the company. Once we have experienced this exact situation with the series of 1on1s to introduce the newcomer to top executives of the company. The idea was bright at the beginning.

However, during the execution, it created some first impression errors for our newcomers among some of those executives which they were also subject to 1st pitfall above. Then, what is the right way to ensure a healthy introduction?

Share the responsibility within key enablers in the company

Encouraging communication is, of course, the right action but you need to make it in a planned setting. Otherwise, relationship dynamics will lead to downsides instead of upsides as the example above.

Before those interactions, you need to nurture your top executives about the objective of the introductions. Set your expectations toward your top executive under these points:

Please do not forget that feed-forward stands valid in that topic as well, so you still need to feedforward your newcomer meanwhile.

Trying to manage the feelings

First two pitfalls are rooted by our expectations that are probably unrealistic. However, this time, this pitfall will belong to our lovely A-player.

Instinctively, she will seek the points that she can feel and show her impact. Of course, there is a lot to do, a lot to fix, a lot to build.

During this hodgepodge, she will pick up some tasks to work on and it will resonate with you the time she proposed. Even though it does not resonate, you might not want to say ‘no’ not to block her/him.

It does seem innocent at first but especially in a hectic environment of a startup, you can lose track of what she is currently on.

In a short period, you can find her working on tasks that you find useless. But it is a significant effort spent already, and you might hold yourself back to intervene, and you might continue to tolerate the point that you can stand. As you wait longer, the harder shake will be needed.

Set certain communication dynamics and checkpoints

Again, the day is hectic and we cannot always create enough space to have healthy communication during the day.

What would be helpful is to agree on 3 points in advance:

These are the common pitfalls that I have figured out so far. As I have experienced similar examples, I observed that it is not one-sided responsibility. Thinking otherwise will be simply undermining our leadership.

Let’s not forget that while we are looking for A-player, A-players are also looking for A-level leadership that enables them.

This article was initially published on Medium.

Arda Köterin co-founded Insider – a B2B SaaS Company – in 2012 and has been operating as VP of Customer Success Team at 26 regions in Insider. He has started his early career in the FMCG sector right after he earned his bachelor’s in Economics and Management at the London School of Economics.