Finding the right digital strategist to join your team is hard. Not only are you hiring in a competitive marketplace, it is incredibly difficult to evaluate the skills of individuals in this space. The word ‘strategist’ is overused to the point that it is almost meaningless. In any given interview for this role, I could find myself speaking with a salesperson or a technologist. And the interview itself is an odd kabuki dance where it often feels like the participants are masking their true selves. So how do you truly evaluate a strategist? How do you determine their skill set? And how do you convince the true strategists to join your team?

The first thing to look for in a strategist is their fit with your broader organization. Fit is tough to evaluate, but it is critical. A strategist can be extremely talented, but if they don’t fit culturally with your organizational values and with the broader team, you’re in for a tough time. The reason that fit is so important in this role is that the strategist is dependent on the broader team for implementation of the strategies they put forward. If they are incapable of working with others, they will fail.

That said, fit doesn’t mean hiring someone that will be comfortable inside your corporate machine. A great strategist brings perspectives and skills that don’t exist in the organization. They are disruptive. They make us a bit uncomfortable. They can be difficult. They challenge us and make us collectively better. But this is not an invitation for prima donna behaviour. Disruption doesn’t mean breaking everything and everyone already in place. This is what makes fit so hard to identify in this role.

Beyond fit, there are two broad sets of attributes to look for; hard and soft skills.

Hard skills are easy to evaluate. Do they have hands on experience executing digital campaigns? Have they built websites? Do they have creative skills? Look for a portfolio of work that they can share. And listen to how they describe the impact of their work. Is it purely in academic terms or do they articulate it in terms of impact on the business? Look for direct experience in a variety of digital channels. You are not hiring a media planner; experience in a single platform or channel does not demonstrate an appreciation of the full user journey and the inter-connectivity of all digital touch-points. If the strategist is more senior, some of these hard digital skills might be harder to demonstrate. But this is why a passion project is so important. Are they able to show you a side-project they have undertaken to keep their skills up to date? Do they have a blog or an active social account that is business focused? Without this, they are likely to have lost touch with the mechanics of digital media and are unlikely to command the necessary respect from your subject matter experts.

Still on the subject of hard skills, beyond the multi-disciplinary experience, look for multi-industry experience. This is easier to find in individuals that have worked in agencies. Those that have worked exclusively on the client-side are less likely to have this type of experience. But multi-industry experience is important because it allows you to borrow ideas from one industry and apply it to another. This is a great source of inspiration and disruption since the tendency of many in any industry is to focus on replicating what has previously worked or what the competitors are delivering.

All that said, if a strategist is missing specific types of hard skills or familiarity with an important platform, that is not a deal breaker. The reason is that if they have the right soft skills, they can be trained.

So what are the soft skills that you should look for in a strategist? We have previously explored the attributes necessary for a strategist, and these remain consistent. They remain someone with confidence and authority, a sense of calm and humility. The strategist is someone with acute emotional intelligence and communication skills and a relentless sense of optimism and enthusiasm. In short, they are the type of person you want to be around and spend time with. Without these soft skills, they will have acute difficulty in being able to connect with clients and peers, to motivate a broader team and rally them around a vision they articulate. Without these soft skills, they won’t succeed as strategists.

If you are able to find a strategist with these skills and attributes, understand that they are evaluating you just as much as you are evaluating them. You have to demonstrate that this is the right fit for them at this point in their careers. What are they typically looking for?

First, they are looking for your to take the process seriously. Distractedly asking them a series of generic questions doesn’t inspire confidence in them that this is going to be the right move. Take a genuine interest in what they are saying. Ask meaningful follow up questions. They are looking to be challenged in an interview because they know that it is an indication that you are paying attention and that their role matters to you.

Second, give them broader insight into the organization. This is a senior and multi-disciplinary role. Treat it as such. Make sure that senior people from a variety of departments in your organization are involved in the process.

Next, make sure you are talking about education and training opportunities. The best strategists are always looking for opportunities to learn, because this is how they increase their value.

Finally, be sure to talk about the vision of the business and the value you are delivering to clients. A strategist needs a clear articulation of the position and value they will represent. Without this, their ability to succeed is greatly diminished. The better you are able to articulate the bigger picture to them, the clearer they will see their role in that and the more emotionally invested they will become in the opportunity.

Finding good strategists is difficult, but it becomes immeasurably easier to find the right fit if you are clear not only about what you are looking for, but who you are as an organization and the value they will be able to deliver within that context.

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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