What Does the Best Version of Your Team Look Like?

By Griffen O’Shaughnessy

It’s a deceptively simple question that every business leader should be asking themselves at least every year.

As leaders and owners, we often have a clear vision of our strategy, where we want to be as a business and even a broad roadmap for how to get there. In some cases, our vision for what our team should look like is less distinct.

There are numerous reasons for this discrepancy, one of which is how little time most leaders truly have to consider future strategy. From the outside looking in, a person might think that a leader or owner would spend a third or even half of their time planning ahead. In its most recent study on the topic, Harvard Business Review noted that CEOs spend an average of 21.5% of their time on strategy. In a piece published on Forbes in 2023, executives were encouraged to spend at least 12.5% of their workweeks on strategy. In my experience, the percentage of time most people spend on mapping out the future is much lower.

The more pressing issue I see in how teams are built is how easy it is to fall into the trap of short-termism in hiring and staffing. It’s hard to blame leaders for this, as they’re as responsible for the effectiveness, productivity and cohesion of the team in the short-term as they are in the future. The decision to focus too heavily on the makeup of the team today and in the near future, however, can hamstring leaders in the future by limiting agility and forcing turbulent and trust-eroding actions like layoffs and furloughs.

The other difficult part about identifying short-termism is that it’s often a result of asking the right, or at least extremely valid, questions about your team:

• If this person leaves, will I need to backfill that role?
• What would happen if we didn’t backfill that role if that person left the organization?
• If I need different skills than what this person brings to the table, should I replace this person with someone with a different skill set? What if the new person brings the skills we need but we end up missing the skill set of the current person in the role?
• Do I need to bring in a smaller number of higher-level, higher-cost people and limit the number of junior staff or bring in a higher number of junior staff members and focus on bringing in only a few higher-quality managers to get the most out of them?
• We don’t have anyone with X skill and we need that skill set to fulfill a strategic priority. How will we afford to bring someone on board if we don’t have any additional dollars for headcount?

All of these questions and more are important to consider as leaders, and answering them can help you make progress toward the effectiveness of each member of your team. But that doesn’t answer the question of what your best possible team would look like. 

Changing the Hiring Conversation From Tactical to Strategic

The light bulb moment for me was when I identified that all of the questions listed above focus on individuals. Hiring is inherently about individuals and as leaders, we absolutely have to get that part right. Where we can go wrong, however, is in failing to look at how every element of individual hiring will affect the company’s future.

That mindset shift alone brings the conversation from “we need to get someone onboarded by the end of December” to a more strategic realm. Bringing a new full-time hire in before the end of the year can provide a useful Band-Aid for a particular problem or problems, but it also has a long-term impact. That salary is now on the books until that person leaves or they are forced to leave. Unless they come in at an extremely high level, they must be offered some opportunity for growth, which adds more recurring costs. 

And if that person is a salesperson, how will bringing them on in a full-time role affect other sales hiring and hiring in other departments for the future? Is it a position you can build around? Does their compensation leave you flexibility for other adjustments or does it mean that person will be your only sales resource for the foreseeable future? How will the new role work with the other teams and provide value to the organization above and beyond a sales target?

This shift is also the reason why I’ve found the “best possible team” to be such a valuable guiding principle, and something to return to when I or our clients are starting to veer toward short-termism. Answering honestly can immediately broaden your view into what’s truly needed and what’s possible for your organization and your team.

To build your best team, you need to understand exactly where your organization is today, where it’s going, and how you plan to get there. From there, building the best team possible is about understanding the competencies you need, when you need them, and what you can afford. Taking the time to review your team at this level can provide you with that all-important balance between aspirational and realistic, helping you understand what’s immediately attainable, what’s a stretch goal and what may be out of reach (at least for now). Most importantly, it will help you set up your team for success in the future, driving decisions based on agility, buffers against unknowns and the experience of your team instead of overindexing against plugging a single hole today.

So ask yourself, if the stars aligned and you could get everything you want, what would that perfect team look like? And remove the obstacles and limitations you may be unconsciously putting on your answers. In 2024 and beyond, your perfect team doesn’t need to be made up of only full-time employees. It doesn’t have to be limited by geography or a commute or office space. It doesn’t have to align to a traditional organizational structure or 9-5 working hours or hierarchical framework. It just needs to work for you and your employees, and it needs to be forward-looking, knowing how quickly things can change.

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At Canopy, we help you build your best possible team, offering access to the very best fractional experts across every discipline. If you’re interested in learning more about how fractional experts and a blended team can work within your organization, we’d love to chat!