Over the last two years, I’ve facilitated about 20 planning meetings across a range of industries and disciplines and have completely changed my perspective on what makes for transformative planning. Ask me five years ago, when I was responsible for a large organization, and I would have said the three keys to an effective planning session are a tight agenda, detailed prep documents, and ample team bonding time.

I’ve now witnessed first-hand that the most productive planning meetings – those that lead to the most creative thinking and ultimately the most significant market impact – are the ones characterized by more listening, more thinking, less prep and less paper. 

My new critical success factors for transformative planning:

Take the time to make the time.

Truly transformative thinking takes time – the team needs to warm up if you will. I’m currently reading a book by Jenny Odell called How to Do Nothing. She cites a 1991 lecture where John Cleese (of Monty Python) listed the five factors required for creativity:

1.    Space

2.    Time

3.    Time

4.    Confidence

5.    Humor

Note that time is listed twice. If your business is currently in “8% YOY growth” mode, a one-day planning meeting may be most appropriate. If you’re intent on transforming your space, or standing up a new organization, or tackling a different customer segment, a multi-day thought-provoking session may be more in order. If you think your team is too busy to take three days off from day-to-day work to think (as someone recently suggested to me), I offer you this: do you have time not to?

Don’t sweat the prep (of documents).

Instead of writing decks, spend your prep time collaborating with your team on crafting a thoughtful agenda. Note each section with “questions to ponder” before the meeting. If you must have paper, limit it to a couple of pages of thought-starters before each section. I’ve also found that if a third-party asks each participant ahead of time what he/she views as a successful meeting, you’ll be prepared to navigate any perspectives that may differ from your own.

Although it may seem efficient, individual work before the meeting, attractively packaged in a long presentation, typically restricts the group to “at the margins” thinking and discourages break-through creativity. If you want out-of-the-box thinking, don’t create a box.

Co-creation is the name of the game. 

Co-creation – asking questions and deeply listening for solutions rather than coming in with a strong point of view – can be scary for many leaders. I acknowledge the fear (of potentially wasting two days with a ticket to nowhere) but point you to the massive upside: co-creation leads to more transformative solutions, a deeper understanding of the “why” across the team, commitment to work as one, and more real team bonding than any dinner or Broadway show. Decide at the outset whether a “tell” or a “co-create” session is more appropriate for where you are in your business. Never try to hide “tell” meetings in “co-create” clothing. If you’re ready to co-create, consider having a third-party facilitator, so you can be an active participant with your team (rather than running the show).

Just a few weeks ago, I worked with a marketing organization to co-create a mission statement — one that meant something. We were faced with a significant challenge. For a good chunk of time, we meandered. Then the leader of the group, who had been standing at the back of the room profoundly listening, perfectly encapsulated the spirit of the team’s discussion into one statement. It became the meeting’s “A-HA” moment and the yardstick against which to evaluate priorities the following day.

It’s best to sleep on it.  

A proven best practice to support creative thinking is to break up your meeting into chunks and incorporate overnight “homework.”Front-load the hard stuff, encourage the team to sleep on meeting discoveries (maybe inspired by a one-page summary of the day’s discussion and some thought-provoking questions), and come back to re-work the next morning. Even if you only have one day set aside for the session, I recommend two half-day chunks, so your team members’ brains can work while they sleep.

Commit to the next right actions, immediately.

If creative thinking doesn’t drive behavior, it’s a waste. Rather than waiting until you have time to package everything perfectly and develop the 12-month roadmap, commit to the next right actions in the room. Then, send out a meeting summary within 24 hours of the session. The 24-hour turnaround will keep the momentum going, and prevent you from generating too much paper.

You are much more likely to arrive at creative, transformative plans if you ditch the planning session. Give yourself permission not to have to know everything and co-create instead. (But, feel free to keep the dinner and the Broadway show.)


  • Rosa Sabater

    President at Martellus

    Rosa Sabater has an extensive background as both a senior executive and entrepreneur. She has led Marketing, Branding, Client Development and Customer Experience functions at American Express, strategic client relations for Booz, Allen & Hamilton, and is currently President and Founder of Martellus, a strategic consulting group. Sabater is also a keynote speaker, meeting facilitator, and trusted advisor, leading discussions on women and leadership for a number of organizations.