How to Turn a Strategy Session from Good to Great

We all use strategy sessions in our projects to some extent. For some of us, it’s a 15-minute regroup, while for others, it is a brainstorming that takes up an entire afternoon. But what is the value of holding strategy sessions, and why do so many of them feel like such huge wastes of time? Is there a way for brainstorming to consistently yield creative results?

The answer is that strategy sessions can be catalysts for creative, innovative, and collaborative breakthroughs, but we often struggle with effectively utilizing multiple brains in the same space.

Although there will always be moments when you hit mental blocks or slow-downs in your strategy sessions, there are certain fundamentals (that we often forget or underestimate) that can keep your strategy sessions on track.

Be at your peak performance

Peak Performance

Speaking of underestimating fundamentals: much like how star athletes will show up to competitions in peak physical and mental health, we as creative thinkers need to be physically and mentally prepared for our strategy sessions. Imagine playing a game of catch where your partner is too tired to participate. Instead of catching the ball and throwing it back, your partner stares blankly as your throw bounces off of his head and falls to the ground. Now imagine your idea doing the same thing.

With so many elements that can throw us off our game, it is important to take control of the basics so that we can effectively contribute to strategy sessions. This means getting a good night’s rest, eating a hearty breakfast, and being in a clear state of mind before we sit down to collaborate. These simple acts of betterment can improve our chances of having great strategy sessions.

Encourage openness, but don’t be afraid of debate

Encourage Openness

Chances are good that if you go into a strategy session with the sole purpose of spotlighting your brilliant idea, you will stifle everyone else in the room. Even if you aren’t an egotistical genius with malicious intent, others will be hesitant to burst your bubble of excitement, and key opportunities for finding better ideas will be missed.

Of course, the answer isn’t to leave your passion and excitement at the door. Instead, try to make your strategy session a space where the presentation of new ideas and lively debate over these ideas are both encouraged and practiced. The key is to listen. Find the best ideas and push each other on what makes those ideas so perfect for accomplishing your goals.

On a related note, dare to challenge new ideas as they come up. Sometimes poking holes in great ideas can help you look through to see even better ones.

Read Also: How To Provide Feedback To Customer Support

Create small goals, but keep the big ones in mind, too

Small Goals

While it is important to be flexible and open to ideas, strategy sessions should have clear, specific goals so that these ideas are focused. There are two important techniques to practice when it comes to setting and meeting goals:

The first is to make your goals small, reasonable, achievable and detailed in their tasks. The goal of “wireframing the checkout process” for a large e-commerce site can be quite a tall order. But if you break up the wireframing process into measurable chunks, such as individual pages in the checkout process, the team can think of ideas to make each page as good as possible. You might also consider focusing on certain elements of your project individually, such as content strategy, user interaction, usability, and then layout structure.

The second, equally as important technique for setting and meeting goals is to make sure that your broader goals remain in the front of your mind. One problem that might come up when setting “mini-goals” is that you will lose sight of the bigger picture. Periodically ask yourself whether you are still doing what you set out to do, and if you aren’t, think hard about how what you’re currently doing is useful toward your goals.

You can improve the focus and the productivity of your strategy session by setting big goals and dividing them up into measurable tasks. Try writing the bigger goal on a whiteboard to help you stay focused. If you find yourself saying, “Oh yeah… that,” when you see that goal, it might be time to refocus.

Maintain momentum by establishing leads

Establishing Leads

Ever heard the expression, “too many cooks in the kitchen?” Well, having too many leaders in a brainstorming session is one of many explanations for why efficiency goes down in group meetings. It’s important to establish a few leads (or point people) early on in a strategy session because they bring order, focus, and direction to group situations; leads can keep the momentum going by acting as instigators, stimulators, mediators, and even decision-makers in group scenarios. But having too many leads will have the opposite effect, causing disorder and stagnating progress.

Make time constraints that push productivity without debilitating the creative mind

Time Constraints

While some amount of time pressure is good, unrealistic constraints are toxic to the creative process in strategy sessions. Brainstorms need ample time to be fluid. But how can you determine the optimal amount of time for pushing productivity without hindering performance?

Consider making adjustments of five or ten minutes to your meetings to gauge how more or less time affects productivity. Seeing the impact of these small adjustments can help you find the sweet spot between pressure-induced brilliance and freedom-inspired creativity.

Eliminate distractions

Eliminate Distractions

Have you ever had that sensation where you knew an idea was trying to formulate itself in your head? You know, the feeling that then promptly forces you to close your eyes, focus intensely, and will yourself to clearly understand the whisper of inspiration? Now imagine someone chewing, incessantly, on shelled nuts beside you. It is hard enough already to stay focused!

As obvious as it may seem (we know, you are not the problem), it’s amazing how much damage distractions, big or small, can cause for the flow of strategy sessions.

Of course, there are the usual suspects: silence your cell phones (especially email/calendar alerts), shut the doors in the room, reduce office background noise, and if you’re going to bring snacks, try to stay away from shelled nuts and loud wrappers!

But more importantly, many subtle distractions can render your brain unfocused. When leading the group’s discussion, don’t simultaneously wipe down the entire whiteboard – clean the board before the session starts. If there are logins required for the resources you want to share, don’t stall the session’s momentum by forgetting your password – login ahead of time and have your tabs ready. Being mindful of smaller distractions can help you minimize the risk of losing focus, or even worse, losing potentially brilliant ideas.

Introduce Objectivity, Bring in Fresh Eyes

Introduce Objectivity

One weakness of strategy sessions is the susceptibility to groupthink. When you have multiple people in a room who are feeding off of each others’ ideas, their isolation can blind them to different perspectives, causing their potentially bad ideas to build upon each other. How can you verify if this is happening, and what can you do to fix it?

Of course, you can bring someone with a fresh perspective into the equation. Bringing in outsiders allows you to benefit in two ways. First, whenever you explain an idea to someone, your whole attention is focused on that idea. This initial explanation can help you clarify and refine your thoughts, often resulting in a leaner, more actionable idea. Second, an outsider’s lack of exposure to the session will allow her to highlight gaps and sources of friction that everyone else glossed over.

You should also consider bringing in the one who (should) know your target audience best: your client. This is especially useful if you already have some ideas in place. By observing the reaction of your client to your team’s current ideas, you’ll be able to assess whether you’re on the right track. If your ideas spark a flow of new ideas from your client, the answer is yes. If not, you will know that it’s time to refocus your approach. Just be sure to encourage your clients to take participatory roles in discussions, and they will provide invaluable insight into your target audience’s point of view.

Follow Through and Take Action

Take Action

You say goodbye and walk back to your car beaming. You have just finished the first date, and you’ve never felt better. The sparks were almost visible as you laughed over dinner. But then you try, and try, and try, and despite both of your best efforts to keep interested, things are just never as they were on that initial date.

After all of this effort to maximize the efficiency and momentum of your strategy session, it’d be a shame if everything slowly fizzled out. So before your creative session is complete, you have to do your best to capture its momentum. What are the final steps you can take to ensure lasting success for your project?
Make a written record of what specific actions need to be taken next. You can base these plans on the small goals you set earlier, but remember to keep the bigger picture in mind.

Put your leader(s) in charge of following up with the team’s tasks, bridging everyone’s collective progress into a focused and brilliant result.
Immediately plan a follow-up strategy session where you tackle any problems you’ve encountered and where you set new goals to keep your project on track for completion.

Unless you can capture the energy and momentum from your successful strategy session, the entire meeting will have been in vain.

Good to Great

Sometimes the most basic adjustments can have incredibly positive impacts on your strategy sessions.

But the best strategy sessions are still difficult to achieve because the elements that make them great are often contradictory by nature. You want leaders who can focus your project, but their guidance can restrict your group’s direction. You want to allow time for creativity, but a lack of deadlines can hinder productivity. The dominance of any one of these aspects can cause your strategy sessions to fall short of their true potential.

By embracing and managing the contradictions between these ideas, you can make your strategy sessions more dynamic, inspiring, and productive. There is a certain ebb and flow between these contradictions, and managing them properly will allow your strategy sessions to yield more consistently creative results.

But if you find that you’re still hitting a wall, then there are probably bigger problems at play, and your strategy session should be brought to a temporary halt. Sometimes creativity needs to grow in isolation. At other times the creative mind needs a break to recharge. One of the most important things to know is when it is time to stop.

Ruben Harutyunyan

Back to top