The Ultimate Guide to a Successful Strategy Session

Preparation for the session


Albina Zhdanova

3 years ago | 8 min read

Companies can run for many years without strategy sessions, and be fine. Yet if they start doing that – they will inevitably see greater success and growth and just overall business improvement. Albina Zhdanova, the COO of Tools for Brokers, shares their insights into organizing a productive strategy session.

We all know how small start-ups or any company with less than ten people in the team work. Quite often, it looks like a waterfall – dealing with and focus on whatever happens today. If it is your case today – be careful and make sure the flow takes you where you want to go. Sometimes, it might lead you in the opposite direction.

We know cases where the company was accidentally led to success – but only to a certain point. To make a real breakthrough, you need to take control of the situation and think beforehand, instead of putting out fires when they already happened. 

An important part of thinking about the future is the strategy session when you take a pause and analyze your business direction. I would recommend doing it regardless of whether it’s just you, you and a business partner, or several top managers in the company.

As a result of the strategy session, you should walk out with a 1 to 3 years business plan, a set of criteria and KPIs you need to focus on, and the core goals and ideas you are going to follow.

Preparation for the session

1) Know your whys. Set the goal and make it clear for everyone. Share what is going to be discussed: company direction, evaluation of progress on the milestones (quarterly or yearly), priorities for the year. 

2) Prepare your team mentally. Find your supporters, introduce them to the procedure beforehand, and exchange your ideas. Discuss the future meeting with a few people and engage them in preparation. 

3) Check for problems you don’t know about. There might be some issues outside of your agenda that your team members are experiencing right now. Ask all participants what they think should be discussed during the session and give them samples of the topics. It can be something like: ‘communication process between tech support and developers’ or ‘HR issues’.

It’s best to limit the timeframe for the queries to be submitted to you: 3 days should be enough to think it through and send over.

4) Analyze the questions after you have collected them. You will see that some topics require thorough discussions, while others can be sorted right now. Fix the minor issues immediately and communicate the results to all stakeholders.

At TFB, we’ve divided everything into strategic and operational questions.
Strategic is everything about the future direction of the company that can have an impact on multiple departments. 

Operational is everything about inter-departmental processes and communication. Such questions are best talked through from different angles – departments – and agreed on the standard procedure moving forward.

For example, we’ve introduced the rule that if someone asks a question in the group chat, they direct it to a particular person using their name. It’s a simple change, but it helped to improve communication significantly. 

5) Limit what is being discussed. We have a fantastic team who are enthusiastic and responsible and always look for ways for improvement. The downside of it during our strategic session was that we had too many topics to discuss. We created a poll where everyone could vote for 3 strategic and 5 operational topics. Voting for your own ideas wasn’t allowed.  

6) Start involving people in the process. Ask everyone to prepare the required information – figures and statistics – to present the issue during the meeting.

The idea might be a collective result of several departments, so each of them might want to present their perspectives on the case. Limit intros to 5-10 minutes with possible graphs and figures, helping to explain the case to everyone. This is especially important for complex topics, such as the direction of the projects you have, or future functionality choice. 

7) Make sure the whole team and company are prepared. Ask your managers to organize their week so that they can focus entirely on the session. It helps if they warn their teams that they will not be available during the session days.

8) Choose a mediator. Is it going to be yourself or an invited person? If you want to do it yourself, be considerate that your goal is to make everyone speak up, and you shouldn’t be the only one talking. In fact – you should be silent, summarising the result and taking the notes.

If you are the CEO, you might think that the decision can’t be made without you. Trust me – if you have a like-minded team, then they will come to the same conclusions that you would. Think about the problems before the meeting, and later, you can gently guide your team with questions and challenge them with “whys” and “what ifs”.

The session

Break the ice. How you kick off the meeting depends on how well people are connected and what kind of conflicts currently exist. In our experience, we had some issues, and our teams were spread across different countries. We needed to address all problems and build trust before we could focus on business. 

What did we do? We have spent the entire first day presenting ourselves to each other, building the connection and bonding. There are several well-known team-building strategies. Whatever activity you choose, please remember that the major goal is for people to open up, speak up, and get comfortable. It’s all about them and their colleagues.

If relationships in your company are already well-established, still make sure some icebreaking is happening. You might do something as simple as asking everyone to select 3 people they would go on a spy mission with and why. General questions about hobbies or work are also great.

It’s also recommended to hold the first (or every) meeting out of  the office: far from computers and daily working environment. This is a small trick that helps our brains think differently and be more open-minded in the new environment.

Intro to the meeting. The moderator should start the day with the opening speech, telling everyone why they are here, what is expected in the end, and what’s going to happen the following days.
You can also mention that nothing is personal. Only ideas are challenged and not the qualities of the members. 

Start by discussing where you are today. We started with a SWOT analyzis of the company. As the next step, we have chosen the opportunities we wanted to use, the strengths we should focus on developing, the weaknesses we needed to emulate, and threats we wanted to protect ourselves from. 

After that, we have set measurable goals for 1 year, and abstract goals for 3 years.

The following questions might help you do that: Where do we want to be? What type of company do we want to be? What should be our values?
Moderator can guide the conversation with pre-planned questions: What about the service level efficiency? Should the company be more or less client-oriented? What results will give us a feeling of satisfaction?

Guidelines and handbooks for employees. Guidelines and handbooks are an essential step that we have created not so long ago.
We’ve had a rather quick jump from a small 10 people start-up to an international company with 70+ employees. When you are small, many things are obvious, and everyone follows the unwritten rules.

It doesn’t work like that in bigger companies, and that’s where the guidelines come into place. Based on our goals and strategy, we have outlined the attitudes towards our work, clients, and colleagues. It is a set of rules that all existing employees follow. This information is also communicated to all newbies. We even discussed it during the interviews to help us hire only those who share our values. 

Daily business. At this point, everyone bonded, completed the SWOT analyzis, and everyone is united by the same goals. Now is the time to switch to daily business topics. 

Share the agenda with everybody and start going through it one by one. It’s better to start with operational questions as they are typically the most annoying ones, and they can also be resolved quickly.

The designated person presents the issue, and the moderator starts asking for opinions on ways to resolve it. It’s important to ask different team members to make sure everyone is engaged and free to share their opinions. Pay special attention to colleagues that speak the least, and don’t be shy to address the questions directly to them. Even if they are not from the department that is being discussed – they will have some handy input. 

Remember: there are people who won’t say anything unless you ask them.

Staying on track. As the meeting progresses, you will notice that some of the questions are connected, and sometimes the thought process leads people away from the subject. 

Don’t let those distractions take over. Focus on your agenda, and keep everything else for later. The moderator should take notes of all new ideas and decisions. It’s a delicate job to stop those team members that keep on repeating the same ideas, manage the argument, and lead everyone to a solution. There will be decisions that not everybody agrees on, and that’s okay. 

Strategic questions. So far, we have spent 2 days working through the operational issues. By the end of each day, the moderator summarizes the results of the previous day and chooses the next question from the list.
It’s time to move to the strategic part of the session. Here the team is brainstorming, coming up with ideas, challenging each other, playing with various scenarios.

You might think about new channels of finding the prospects, what product should be delivered next, and the stages of its implementation. At this point, long-term goals are discussed, so it’s important to assign the responsible person for each of them.

Finishing up the session. On your last day, it’s better to finalize all discussions before lunchtime, so that everyone can have a meal together, mingle, share the experiences and emotions.

The work doesn’t stop once the session is finished. The next step is preparing the doc with a summary of the notes. The doc should later be shared with everyone, along with thanking them for their contribution.

Next steps after the session

The work isn’t over after the session is finished. Follow up activities are just as important as the event itself. 

1)  All decisions must be written down and shared with employees, and all the new rules should be actioned. It will take some getting used to, people will probably stick to the old ways, and it’s okay – get back to them and talk it through.

2) Long- term goals must be written down, broken into small steps, and have a responsible person assigned to each of them. It helps to use a project-tracking or task-management system that fits your requirements.

3) It is the job of the operational director to track the results, catch up with team members, and check the progress afterward.

4) The optimal intervals for follow up meetings are every 4 months – just before the seasons, and not too often at the same time.

We had the first strategy meeting in early February, second follow up meeting in May, and third in September. In our industry, these months are seasonal, so they fit perfectly for overlooking the whole company performance. 

In those meetings, we repeat the goals once again, assess how far we have come, examine previously made decisions. We ask ourselves: Do we follow what we’ve agreed on before? Is our plan up to date? What results have we achieved, and do we need to make adjustments?

Then we talk about long-term plans and projects. Responsible employees report on the progress made and on delays (if there are any). We also set the target for the next session and until the end of the year.

5) After this meeting, you make an updated summary with the latest progress, points that were discussed, and the conclusions. These documents are saved by the project management team and can be referred to at any point.

This concludes our guide to a perfect strategy session. Some parts of it may be more relevant to your company than the others. You should make it your own and remember that the ultimate goal is your company’s success. 


Created by

Albina Zhdanova

COO in Tools for Brokers







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