Offsite meetings have a checkered past. Back in 2006 a colleague shared this painful article with me.  To quote from the main article:

“…only about 10 percent of executives consider offsites truly valuable. Half said they aren’t worth the time or money.”

Over the last 7 years I’ve seen the exceptionally high value offsite meetings can bring but also the stress and pain that often leads up to them.

At my last employer, the entire global executive and senior management team would have a 6-monthly operations review offsite that ran for 3 days. We booked out significant portions of a large hotel in the US and fly the entire team together from over a dozen sites around the world. Over 3 days, the leaders from each site would present their statuses, finances, roadmaps, portfolios, visions, strategies and plans to a group of about 50 of us. We’d put them under the grill and review their work in depth both as bosses and peers.

We’d take time to focus on specific strategic issues that benefitted from face-to-face focused collaboraton. (When your management team are distributed around the world. A few intense days of co-location often delivers far more decisions and clarifications than 6 months of project work and conference calls.)

The general approach for these was: Prepare, Pitch, Review, Collaborate, Revise, Re-pitch.

Sounds pretty sensible? – It is…        … if you know what you’re in for. 

The offsite workouts were usually brutal but exceptionally valuable. By the end of the week everyone’s plans were in far better shape, we all understood what each other were doing, found areas for shared benefit and made a lot of difficult decsions.

Better still, we spent a few days working, eating and drinking together. 3 days of deliberate convergence in order to stem the behaviour issues associated with extreme divergence kepts us functioning as a successful management team.

Whilst the outcomes were great, they took their toll. The pain behind the scenes generally involved a bunch of us working 2 weeks of long evenings and weekends to pull all the data, presentations and spreadsheets together. ($100m of software projects contain a lot of moving parts & data) Often we’d still be revising our work during the start of sessions and whoever went first bore the brunt of painful lessons and questions whilst everyone else frantically updated their slide decks to accomodate the new knowledge.

And here’s the thing – the lines of questioning…

Our Senior Exec at that employer was an exceptionally sharp, experienced, bright guy. After working through multiple iterations and having joined the operations team on the organizing side of the offsites I saw what made him tick. He had a brain full of powerful questions that he’d learned from experience and was constantly adding to them. He knew what to ask and when that would lift the lid on just the right barrel to find a body (if there were bodies to be found).

As a spectator, sometimes it’s satisfying seeing the blood on the floor when someone you think is an ass-kisser takes a roasting. It’s not so fun when it’s your own team.

I even helped develop a set of “difficult questions” for our Head of Operations in the weekend prior to one of these offsites. They were great questions to ask. The thought and effort put into developing them was a lot like spending an hour writing test cases up-front. We learned quickly what we really needed and wanted to know (and why). We were confident we could get under the covers of even the most prettied-up project report.

But we could have made the whole thing so much less brutal.

Much like writing test plans, if we’d just put the questions out for participants to review in advance they’d have adjusted their research and reporting to accommodate them rather than playing project question battleship on the day.

So here’s an action for you.

Next time you’re reviewing a project or a piece of work, capture the questions you regularly ask.

Now…

Share them

Share them with the people you’ll be asking beforehand.

Now they can answer those questions sensibly first and you’ll all have time to dig into more valuable insights.

I have a few more posts planned around “critical questioning”, plenty around running offsites and I’ll be sharing where I’ve been for most of the last year so keep your eyes open for more soon.