5 Top Tips for Effective Team Planning Sessions

blog Jan 29, 2024

Why are planning sessions so crucial to your team?

There’s a reason why Simon Sinek’s Start With Why upended the world of leadership and business when he hit the mainstream with both this talk and the book.

For a long time, the focus in the workplace was on outcomes without connecting their people to the why of those outcomes. We soon realised by using Simon’s framework, that connecting people to the core of why the business exists and exactly how their role impacts the world created stronger relationships, better outcomes, and more innovative thinking.

A fundamental aspect of connecting your people to your business why is running effective team planning sessions. From this connection grows a rich dynamic for your team – but without a well-structured planning session you could be missing out on leveraging the best from your people.


People want purpose.

People want clarity.

People want to belong.


Understanding these driving motivators, and planning sessions are a great opportunity to bring the whole team on the journey forward. Engage your team. Invite their input. Share your big ambitions. Validate their challenges. Spend time on solutions – but spend more time listening. Get to know your people. Set goals. Set timeframes. Brainstorm potential roadblocks. Thank them.

These sessions can help ensure everyone is on the same page and working towards the same goals. This in turn improves communication, collaboration, and overall team productivity. Effective planning sessions can also help to identify and allocate resources, prioritise tasks, and track progress, which can help to keep the team organised and on track.

Team planning sessions not only provide an opportunity for team members to coordinate their work, but they also allow business owners to learn about their people and gain a deeper understanding of their interests, skills, and passions.

During these sessions, team members are encouraged to share their thoughts and ideas, which can provide valuable insights into their strengths, weaknesses, and areas of expertise. Additionally, by actively listening to and engaging with their team members, business owners can identify any potential training or development needs and create opportunities for growth and advancement.

This knowledge can also be used to better support team members by assigning tasks that align with their interests and strengths, which can lead to increased motivation, engagement, and job satisfaction. Furthermore, by leveraging the interests, skills, and passions of team members, business owners can create a more productive and innovative team, which can ultimately benefit the overall success of the business.

Overall, planning sessions can be a vital tool for maintaining a cohesive and efficient team.


When should you run a team planning session?

If you’re new to running team planning sessions, or not quite sure when the best time is to run them, here’s a quick recap of the typical timeframes for these kinds of sessions – but ultimately, do what is best for your business and your people.



If you do no other planning, at the very least run a well-structured annual planning session that involves your whole team.



A mid-year check-in can help you and your team identify successes, earmark challenges and weed out any issues that could snowball if left unattended.



Quarterly planning sessions are a great way to keep both you and your team engaged and looped into the goals and objectives outlined for the year. It can also help you mitigate any problems before they take flight, pulse check your team and generate innovative solutions throughout the year.


Identify your business cycle

If your business doesn’t fit into annual, bi-annual or quarterly cycles, think about the cadence of your business cycles. Is it seasonal? Does it follow the calendar year or financial year? Work with this cycle instead of against it.


Never run a planning session? We dare you to run one in the next 30 days.

If you’ve never run an effective team planning session before, we challenge you to run one in the next 30 days. The best way to learn is to do.


We have our top 5 tips for running an effective team planning session in the next section so you know exactly what to do.


Top 5 tips to running an effective team planning session.

It’s all good and well to say run an effective team planning session… but exactly how do you do that?

Here are our top 5 tips for running an effective team planning session.

  1.  Align with the personality of your culture.

Don’t try to be Google if that’s not the culture of your business. Consider the individuals on your team and how they like to engage. Are they mostly extroverted, introverted or somewhere in between? Do you have neurodivergent team members? This allows you to design a structure that accommodates the different learning and work styles of your team. A great resource is the DiSC Assessment which gives you and your team greater insight into their personalities at work.


  1.  Make it more than business targets.

Include team-building activities, and add movement and games in between dense sections. Try running certain sections while standing. Plan a team lunch or dinner afterwards. Cater if your meeting is longer than an hour or two.


  1.  Communicate clearly.

Clear is kind, unclear is unkind, as Brene Brown says. Be crystal clear at every stage of the planning session. From the agenda and outcomes to the vision, mission, to budgets, constraints, and whatever else impacts your business and your people. A good rule of thumb is if you can’t explain it to a seven-year-old – you need to make it simpler. Run your notes through the Hemingway App which tests the literacy level of your content.


  1.  Mix up the format.

Team planning is about the team. This means giving your team plenty of opportunities to be heard throughout the session. Incorporate small group activities, individual reflection, and anonymous feedback mechanisms. Invite someone from your team to run a particular section. Move the location outside of your office or consider an external facilitator.


  1.  Clear action plans and follow-up.

There’s nothing worse than coming out of a planning session all riled up and ready to rumble… only to forget who’s doing what, whether that thing was confirmed… or where are the notes from this section of the meeting? Ensure that you communicate the outcomes from the day and an action plan in a clear and timely way. And don’t forget to thank your team for showing up.



Running an effective team planning session is a vital skill for leaders at all levels of organisations whether you’re a team of 2 or 200. Investing time and energy into running planning sessions well can set your business up for success over the long term – and is a great way to stay connected to your team, and keep them connected to each other.


While there’s no one way to run a successful planning session, use our top 5 tips for running an effective team planning session to make sure that you hit the right balance of connection, community and clarity.


If you’re struggling to run effective team planning sessions, book your free 15 min HR consult with our expert, Kristy-Lee Billett.


An invitation to join a thriving business community

If you found value in our tips for running effective team planning sessions, I’d love for you to join us inside our free Facebook Group where you can connect with other like-minded business owners, leaders and managers to discuss topics like this, and all things HR - https://www.facebook.com/groups/hrsupportaustralia


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