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Les McKeown's Predictable Success Blog

  • October 8, 2021
  • minute read

5 tips to make your strategic retreat a success 

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A version of this article first appeared in Inc.com

Listen to Les McKeown read this blog post:

As we've been exploring in recent posts, it’s that time in the calendar when every growth leader’s thoughts are increasingly fixated on…next year. 

And that means many of us are currently engaged in that traditional late Q3 / early Q4 event: the oft-dreaded retreat to plan next year’s strategy.

Sadly, apart perhaps from ‘performance assessment’, no two words are more likely to induce acid reflux and facial tics in an otherwise well-balanced and competent executive than the phrase ‘strategic retreat’.

What should be a valued – and enjoyable – opportunity to escape the grind of day-to-day tactical implementation and spend time thinking and planning at a strategic level, so often instead becomes a plodding, dry exercise in death by powerpoint; an endless sequence of presentations that cram too much information into too little time, inducing in even the presenters a sense that they’d prefer to take a paper clip, straighten it out and stab themselves in the eye, rather than sit through another hour of this mind-numbing navel-gazing.

Having participated in hundreds of strategic retreats, I know that this doesn’t need to be so. Here are five ways you can make this year’s strategic retreat a resounding success:

1. Don’t hold it on a Monday 

You want your participants to arrive at the retreat clear-minded and able to focus – so don’t hold it on a Monday (when everyone has forty-seven things they need to communicate to others so they can start their week right, plus a looming mass of issues that arose over the weekend); or on the last day of the month, when everyone is racing to hit their quotas, or on any other day that requires the majority of people’s attention to be elsewhere.

Instead, pick the least event-laden day you can find (likely a Tuesday, Wednesday or Thursday in the middle of the month).

2. [For in-person retreats] Go off-site 

Do yourself and everyone else a favor – find an offsite location, far from the office, and preferably with spotty Internet access.

If your team is clustered in a conference room at head office, the likelihood of interruptions (and the probability of disengaged participants ‘finding’ an emergency to deal with) is too high. Poor Internet access removes the temptation to ‘multi-task’ (read: disengage).

2. [For Virtual Retreats] Strand the Retreat over Multiple Days

If like many organizations, you're conducting your strategic retreat virtually - do you and your team a huge favor - don't try to do it in one marathon session.  Virtual sessions lose their efficacy at a scary rate after 2 hours, and are sub-optimal after 3.

Instead of trying to jam the whole thing in to one day, strand it over three consecutive days, with session of 2 hours each.

3. Get a seasoned facilitator

Find someone from outside the company who is experienced in dealing with C-level executives to facilitate your retreat.

This doesn’t mean yielding the overall goals of the retreat to them – you still must set those – but it does mean entrusting them to manage the process of achieving those goals.

Why bring in an outside facilitator? For one over-riding reason:

To engender rich interaction by leveling the ‘status pyramid’. 

Un-facilitated retreats tend to be heavily influenced by the status of those in the room, with discussions (and the resulting decisions) skewed by the relative position in the org chart of those who are contributing.

A skilled facilitator, unencumbered by the subliminal influences of where he or she fits on the org chart will create a more neutral environment in which everyone can contribute co-equally, and will encourage a stronger challenge factor in a non-threatening manner.

4. Make pre-reading mandatory 

In most strategic retreats too much time is spent on presenting information, and not enough time on analyzing and acting on it. Make it your goal to reverse that situation: Have whatever presentations and background reading material are required for the retreat made available at least one week ahead of time, so that all the participants can read and digest them ahead of time.

Start each session with the presumption that that the underlying information has already been read by everyone, and use the time for analysis and decision-making, not presentation.

5. Pre-schedule implementation accountability 

Most strategic retreats bring with them an unfortunate reminder: “Gosh, look at these great decisions we made last year – and the year before that – and never actually implemented!“.

The looming shadow of previously unimplemented strategic initiatives can produce a sense of guilt – or at worst, impotence – that undermines the ability of the leadership team to take the process seriously: a disempowering cycle kicks in whereby the trail of inaction from previous year’s retreats shrouds this year’s retreat with an air of implausibility.

Break the cycle by pre-scheduling post-retreat accountability sessions – 45-90 minute conference calls to discuss the progress of action points arising from the retreat. Schedule the calls monthly for the three months immediately after the retreat, then quarterly after that.

(Hint: Initially, schedule everyone to participate so the sessions get into their diary. After the retreat, the list of actual participants can be whittled down as appropriate, depending on content and subject of the agreed action points.)

What about you? How do you plan your strategic retreats for optimal results?

Let me know in the comments below!

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