Author:  Yurii Gladky

How to hold a strategy session

Several years ago Grape switched to Scrum for managing all of its projects. This framework suggests a small team with no hierarchies that collaboratively address complex issues and find creative solutions. We also use this system during our strategy sessions - both for our clients and within our team. Usually, we split a strategy session into 2 days: the first one deals with inside processes, work algorithms and the team itself, while the second one is focused on the ‘outside’ work with products, marketing strategies, sales rates and partners.

Every month we organise around 3-4 strategy sessions for our clients. This is why, using our experience and knowledge, we decided to create this quick guidance on how to hold a strategy session for your team.


  • Put someone in charge. You will face a bunch of organisational issues while preparing for a session. This is why I advise you to appoint someone who will be responsible for this event from the start. Preferably, one of the session’s participants.
  • Decide on the time. A strategy session requires the involvement of top management, hence I recommend choosing several dates 3-4 months in advance when all of them will be able to leave their tasks and focus entirely on your company’s strategy building.
  • Book a space. Even though Grape has a hub within its office, we prefer to hold our strategy sessions on a neutral territory, where no one could be distracted by quick work questions.
  • Make sure you have everything you may need. During a strategy session, you will need things like a projector, a flipchart, stickers, markers etc. I always advise having extra.
  • Create an agenda. To make sure you have enough time to cover all the topics, you should develop the structure of a session. Personally, I divide everything into 3 sections: approximate start and end of working on a block, a name/description of a block, time for a topic discussion in minutes. In this way, you will prepare navigation that will help you manage your schedule when you run overtime (and trust me, you will!).
  • Decide on the timing. From my experience, the duration of a strategic session should not exceed 6 hours. This includes lunch and coffee breaks. Most importantly, try to schedule it in the morning when your team has enough energy to be fully involved in the process.
  • Choose a moderator. If you do not have a person with such experience in your company, invite someone from outside. It is essential that he/she is connected to a topic you want to focus on.
  • Select participants. You will need people who make crucial decisions in your business development in this session. It would be perfect if the number of members did not surpass 8-10 people so that you have time to hear out the vision of each of them and to have a constructive debate.
  • Pick an assistant. An assistant’s job is to help a moderator by taking minutes, working with handout materials, processing information etc.
  • Gather analytics. The effectiveness of a session depends on from data you will draw planning your company’s future and what you want to achieve at the end of a session. The foundation for your new strategy may become an analysis of your performance in new industry sectors, a list of potential areas of growth or the amount and quality of clients coming.


  • Punctuality. Teamwork is one of the most crucial elements of any strategy session, thus there is no point waiting for those late and disrupt a logical course of a meeting. Start without people who did not come in time and bring them up to date as they arrive to discuss the questions left.
  • Neutrality. If you were chosen as a moderator, you must not try to impose your views to the rest of the group. You are either moderating a process or participating in discussions.
  • Focus. Leave all your gadgets and anything else that can distract you from a topic of discussion.
  • Maximum presence. Don’t lose time on the breaks. If your space allows you to put beverages and snacks close to participants, use it. People can also leave a room when they need to, do not stop because of this and make everyone wait.
  • Celebration. It would be perfect to celebrate the outcomes of a session in the end. Going to a bar or a restaurant is a perfect way to reward your team for productive work.


  • Set a date when you should receive all digitized materials from a session and a final document with strategies, tactics, deadlines and people responsible for their implementation. Ideally, you should receive all of these within a week after a session.
  • Do the homework you were given during a session. For example, last year, we had to create an updated price list and a new portfolio of services, redesign our brand’s website and start to work on the agency’s budget for a new year.
  • Share results with the rest of your team, tell them what are the future strategies for your brand’s development and who will be involved in what areas. You should also decide on the qualitative and quantitative success indicators of their work.

A strategy session is a powerful tool to involve your team in the evaluation and planning of your company’s development. I recommend that you make it an annual practice, prepare for it in advance, bring to life what you have come up with during those sessions and last but not least celebrate the results with your team over a glass of whisky sour and Negroni.

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