Herding Cats

Episode 73: Herding Cats – How To Lead A Team Of Strategists

Independent. Contrarian. Brilliant. Difficult. Nimble. Aloof.

The digital strategist may be a multi-disciplinary octopus, but in our everyday skins, we can also resemble our feline friends. We like to work alone and on our own schedule. We don’t like to follow the direction of others. We can come off as arrogant. We sometimes chase shiny objects. So how do you keep a team of strategists focused on working together, working within a broader team and delivering the best work that they can?

Let me start by stating that I am a cat person. I like their independence, their spirit, the fact that they are undeniably predators. So the comparison to strategists is an affectionate one. But there’s no denying that the cat, like the strategist marches to the beat of its own drum, and as such is notoriously difficult to lead.

Understanding how to lead a team of strategists begins with recognizing what motivates us.

Strategists are motivated by the opportunity to solve complex problems. We need a variety of experiences in order to constantly learn. We recognize that over time we lose touch with the mechanics of the execution, and we compensate for this through variety of experience. The value we bring is as generalists, so we need enough experience in order to truly be that. We need an environment of continuous education. We also need a workplace that allows us to experiment in new areas, either directly or indirectly through our colleagues. In short, we need space to learn, to break things and to fail.

The value that strategists deliver is dependent on getting the broader team to execute against the plan they develop. That makes the value that we deliver somewhat nebulous. So a critical motivator is the need for acknowledgement that the work we do is important to our clients and peers.

Since strategists are generally on the periphery of a broader team, we are often overlooked and not included in regular discussions. We can feel out of the loop and sometimes out of step with the broader organization. We need to feel included within the rhythms of the organization.

Finally, strategists don’t only look for growth in experience, we look for career growth and development. Since we are multi-disciplinary generalists, it can be hard to clearly define what this career growth should look like, even to ourselves. Rather than clearly defining each step in that career, we need the freedom to develop our responsibilities as the opportunities show themselves.

Given all that, what are the mistakes managers generally make when leading teams of strategists? Because strategists don’t fit into a neat tactical and task driven box, they often make managers uncomfortable. Their value and contribution is not acknowledged. They are given repetitive tasks that are not intellectually stimulating. They have no time to think, to experiment and to learn. They don’t feel that their manager will back them up if they make a mistake. There is no clear opportunity for career development. Strategists feel cut out of the broader communication of the team.

I recognize these as managerial failings because I have experienced them myself as a manager. In my time leading a team of strategists, I’ve made all these mistakes.

So what have I learned about how to lead strategists? I’ve learned that communication is incredibly important. You need regular conversations with your team. As part of these conversations, you need to give them the room to share ideas, to vent frustrations and to discuss challenges. You need to check in on their work regularly enough that they feel valued, but not so much that they feel micro-managed. You need to give them the authority and freedom to make decisions. They need to know that you have their back, and when they make a mistake you will take collective responsibility for it. They need the opportunity to carve their own careers. Above all they need freedom to learn and test and break things and put them back together in unorthodox and unexpected ways. And they need your clear support in how to develop their careers.

Strategists need enough direction to know you care, enough support to know they are valued, and enough freedom to make their mark. Give them a goal to strive towards, the room to learn and the support when they need it, and you can call yourself a cat herder.

Next week on octopus, we will continue to explore the role of the digital strategist. Please be sure to comment below. I’d love to hear from you. Please subscribe for alerts about new episodes and content. Thank you for listening to octopus. I’m Nasser Sahlool.

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