Strategy, brainstorming facilitation, and CEO coaching in Ojai, Ventura, Santa Barbara, Los Angeles

Posts from the ‘Strategy’ category

I first wrote this article 10 years ago, and recently came across it in my Evernote files. Since then, I’ve graduated from working inside growth companies to coaching CEOs of growing companies, and I’m in the process of graduating from track days and time-trials to door-to-door racing. Reading the article 10 years later, I realized these same lessons ring true, and that I’ve learned a few things along the way, so here’s version 2.0. Enjoy!

I love analogies, but for years I’ve listened to my colleagues in Canada relate every business lesson to a hockey analogy. Everything will work out fine if we just “skate where the puck is”. Working now in the US, everything is a football analogy – “we need more team members who are broken-field runners”. I do enjoy hockey and football, but I barely know the difference between an offside and icing let alone who won the Stanley Cup in ’72. Half of the time the analogy is completely lost on me.

So in an effort to bridge the communication gap, I’ve related my learnings in business to one of my passions – auto racing. I hope this helps other business-minded gear-heads communicate more fluently with their peers, and if nothing else, I’ve laid the foundation for you to take your team to the Skip Barber racing school for “team-building”.

Look where you want to go
One of the deadliest errors, often made by beginners on the racetrack but occasionally made by experts, is called “Target Fixation”. In a moment of high stress, your brain is so overloaded that it becomes fixated on exactly what you are trying to avoid – gravel in a corner, an obstacle, or another car. You end up hitting it square on.

In business, it’s very easy to get fixated on what you don’t want – losing a key customer, a market downturn, your best performer leaving. More often than not, you run straight into what you were trying desperately to avoid. It almost happened to me in a previous business in the so-called “Great Recession”. Around 2009, our pipeline was drying up, and in a sombre management meeting, we told ourselves “I guess we’d better start planning to downsize”. Luckily, one of our mentors snapped us out of it. He wouldn’t let us even mention downsizing until we had exhausted every possible option for filling up our project pipeline and hitting our revenue targets. It was every man on deck. He refocused us on the positive outcome, and guess what, we turned it around and headed straight into our best year in history.

To be a great auto racer, you need to have “wide eyes” – you learn to look far ahead, use every corner of your peripheral vision, and look where you want to go. Being a leader is no different – your job is to look further than tomorrow, get a lot of advice and input, and keep your team focused on where your business is headed.

It’s a mental game
Time and time again, I hit a plateau at the race track. I think I’ve wrung every last bit of performance out of my car and driving to my absolute abilities. Then I invite a very fast, very experienced driver to drive me around the track in my car. After a warm-up, they do a few blistering hot laps, a full 2.5 seconds faster than I. We returned to the pits, review the session, and he sent me on my way. The very next lap, I was 1.5 seconds faster, and the next 5 laps I was consistently 2 seconds faster than my previous laps (I’m still chasing that last few tenths, and that’s what makes racing so fun). It wasn’t the car, or even my abilities that was slowing me down – it was my mental model of what was possible.

Success in business has a lot to do with your mental attitude. Studies have found strong correlations between entrepreneurs with positive outlooks and business success. Most of the time, it’s not your competition or the economy that’s holding you back, it’s your own attitude and beliefs. Those that have an attitude of abundance generally outperform those that believe the glass is half-empty.



A minor shunt. It’ll buff out.

In racing, no matter how practiced and prepared you are, you can suffer dramatic setbacks. Parts break, someone bumps you, or for whatever reason, your perfect setup just isn’t working on a particular track like you thought it would. Even world-championship teams have bad weekends. The best drivers have persevered through dozens of bad weekends. They learn, they adjust, and they go try again.

The business press loves the “overnight success story”. What they fail to mention is that behind almost every business success is years of blood, sweat, and tears. Yes, one day they break through, but often these overnight success stories have been at it 10, 20, or even 30 years before they became a household name. Every business had failed starts, bad sales calls, unproductive employees – you name it. Things that are completely out of your control hit you from left field. The only thing you can do is dust yourself off and keep going. So much of success in business is just showing up and trying. If you’re self-aware and inquisitive, you’ll learn with every setback, and one day you’ll wake up amazed at the progress you’ve made.

Change one thing at a time
There’s a popular business mantra that says “you can’t manage what you can’t measure”. I also believe that to measure change, you can’t change everything at once.

In a growing company, you will always looking for things to improve. As you grow, you’ll find it increasingly difficult to apply measure progress when you’re changing so many things at the same time.

In racing, we only change one thing at a time, and test it’s effect. You change your sway bar settings on one end of the car, and you go test. You adjust your shock absorber rebound, and you go test. If you were to change all those things at once, and you spun in turn one, you’d have no idea what caused it, and lose precious hours going back to square one.

The same is true whether you are changing a business system, or changing an attribute of your product or web site. If you change your customer acquisition strategy, launch a new web site, and restructure your sales team all at the same time, you’ll never know which one moved the needle.

Win together, lose together


Coaching session with

Even at the amateur level, successful racers have coaches and mechanics. At the professional level, teams spend an enormous amount of time learning to work together in perfect harmony. They know that everything, from the pit crew who refuel the car in seconds, to the suspension engineer who knows exactly how to set up a shock absorber for a specific track, have to come together flawlessly to win a race. Lewis Hamilton gets most of the press for winning 6 championships, but what impresses me most is how Toto Wolff and his team coordinate and motivate the hundreds of people that work behind the scenes to build and maintain a winning race car.

New leaders often believe they need to have all the answers. It’s ok to tell your team “I don’t know. I’m not an expert in this area and I need your help figuring this out”. On top of that, there is probably someone, somewhere who has gone through exactly what you are going through who is willing to help. In my career I’ve been lucky to have a few people who were willing to sit down and talk through a business challenge for nothing more than a latte and the promise to pay it forward.

Successful management teams are staffed with people who compliment one another’s strengths, and who think differently from one another – some big picture thinkers, some detail-oriented; some who are engineers and some who have arts backgrounds. Believe me, it’s not easy – you’ll disagree constantly, but in the end you’ll make better decisions because they’ve been dissected from every angle.

The really successful teams invest time and money learning how to communicate better and work better as teams. They set aside personal ambition and break down silos to achieve a shared vision. Like a championship race team, great teams are built with trust, shared respect, and communication.

If everything feels under control, you’re not going fast enough
World champions drive their cars at the very edge of control. A little more steering input, or a fraction more throttle, and they would go careening off into the weeds. It’s a strange sensation, to feel almost completely out of control, but at the same time, completely in control. Legendary driving coach Ross Bentley calls this “being comfortable with being uncomfortable”. The flip side of that coin is that once and a while, you will spin out (ask me how I know).

If you’re an auto racing fan, you’ve witnessed the two extremes – on one hand are the wildly aggressive drivers that lead one race by a half a lap, but crash out in the next one. They burn their teams out and burn their bridges. On the other hand are the backmarkers who are unwilling to be as aggressive as the winners. Champions find that perfect balance – they are blisteringly fast, take calculated risks, but are patient and persistent, tracking their opponents lap after lap, waiting for them to slip up so they can take the pass for the lead.

In business, I’ve seen companies who are unwilling to take risks, and unwilling to live on that edge of controlled chaos, and they usually plateau. I’ve also worked with companies that are in constant chaos, where the leadership team leaves burning bridges, burned out employees, and fried customers in their wake. The perfect flow is right down the middle – taking calculated risks, moving quickly, and working right in that zone where things feel a little out of control.

You’ll never have all the data and all the answers – a napkin-sketch plan passionately executed will beat a perfect plan poorly executed every single time.

Slow hands, fast car

The final, and most difficult lesson to learn for executives and CEOs is to lead with calm, patience, and perseverance. In a race car, it looks impressive to be attacking every corner beyond the limit, sliding the car, hands frantically correcting and sawing at the wheel. Typically this racer runs out of tires, or talent, and loses their lead to someone smoother. The same goes for business. The model we see on TV reality shows is the frantic, yelling CEO, driving everyone to the brink and leaving a wake of destruction. In real life, it’s a marathon. The toughest lessons for me personally, both on the track and in the boardroom, has been to remember to breathe, to listen, to seek to understand, and to slow down time when everything’s feeling out of control. The best leaders lead with grace and build confidence in their team, and are aware of the wake they leave.

And remember, if you’re still stuck on your hockey and football analogies – as Hemingway (or Ken Purdy, or Banarby Conrad, depending on who you ask) once said  “There are only three sports: bullfighting, motor racing, and mountaineering; all the rest are merely games.”

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Your last strategy session felt like a waste of time because it probably was.

We’ve all been there – we get an email announcing the next corporate or product strategy session. It’s at the local country club. There will be a nice lunch served, and possibly cocktails after. There will be flip charts and markers. We’ll get out of the office, away from the day-to-day, where we can think clearly. What could possibly go wrong?

You start out strong, maybe even do a SWOT analysis. Then a long-standing disagreement between the VP Sales and the VP Engineering erupts, and before long, you’re way down a rat-hole and running out of time. In the end, you end up either following the CEO’s lead, or you agree to “come back to it”. Everyone leaves with the slightly uneasy feeling that comes from everyone having a slightly different interpretation about what you’re doing next, and what’s changed.

Fear not, for there’s a better way. Many strategy sessions miss at least a couple of what I call the Seven Commandments of Strategy. Catchy, right? They even begin with “F” for effect. I was thinking of calling them the 7 F’ing Commandments of Strategy 🙂

Forward planning

I can’t tell you how many planning sessions I’ve either attended, or colleagues have attended, that are planned a week, or even a day, before. And choosing the venue and coffee break menu doesn’t count as forward planning. Strategy is a process, and the following six Fs need to be planned in advance. As a general rule of thumb, I feel it takes at least 4 hours of prep for every person hour you’re going to spend in your strategy session. The good news is, you don’t have to do that all yourself. Some of that is fact gathering, which your team will help with, and some of that is planning the process, which your facilitator can help with.

Start with the outcome in mind, and work backwards from there. More on that when we get to Focus and Framework – I’m getting ahead of myself.


So much time in strategy sessions is lost arguing about facts, like how much revenue did we make in a given segment last year? What did we spend on Project X? If you don’t have these numbers at your fingertips, you’ll either spend precious time looking for them when you should be discussing strategy, or you’ll waste even more time having emotional arguments not based on fact.

If you want to calculate the ROI of doing fact-finding before the strategy session, rather than during, take a look around the table and tally up the fully-loaded, per-minute cost of all the salaries around the table. Hopefully you’re now hyper-aware of every minute you’re wasting trying to find last year’s Asia-Pac numbers.


A good facilitator is worth their weight in gold – hug a facilitator today! Go on!

A facilitator is not the CEO, or even the VP Strategy. It can’t be someone who’s actively involved and emotionally invested in the business or product. Facilitation is part science, part art, and a full-time endeavor.

The role of the facilitator is to make sure the session meets the stated outcomes, the team follows a process, the session stays on track and finishes on time, that everyone who has something to say is heard, jolt thinking and break the team out of their usual patterns, inquire for deeper understanding capture the results and proceedings, and help process the outcomes. No matter how much you consider yourself a multi-tasker, you can’t be fully engaged in something as important as deciding your future, and trying to facilitate at the same time.


Too many strategy sessions try to cover too much ground. “We’ll leave here having clarified our vision for the product line, articulated a platform strategy for the 1, 3, and 5 year timeframes, carved out a go-to-market strategy, and have a detailed plan for going forward” is a typical goal statement at the beginning of a session. Best case, you’ll probably get, at most, two of those done. Pick one or two major objectives for each session, such as defining your top 3 strategic goals for next year and creating a 1 year plan. Strategy is a year-round process, and you can’t expect to clarify vision and strategy, and complete all your planning in a matter of a couple of days. Split up your strategy sessions over multiple sessions throughout the year with different themes. You’ll be more focused, more productive, and you’ll get more done.


Strategy is intense, and it should also be fun. This is your opportunity to lift yourself out of the day-to-day of running your company or product team, and explore the crazy ideas that could be a turning point for your business, or an idea for a new product line, or simply an idea that will spark other ideas. There is a ton of research that shows that people think more creatively when they are happy and having fun, and there are a number of ways to make your session more fun and productive – things like Gamestorming and Innovation Games. Strategy should be all work AND play.


Strategy has been studied so extensively, and so many interesting strategy processes created, that there’s no excuse for winging it. Using a framework helps you organize your session, know what background homework you need to do, and gets everyone’s head in the game prior to your session. There are a number of methods, depending on what you’re trying to tackle, and I’ll go into some of them in more detail in later posts. A few to explore: Blue Ocean Strategy for creating truly differentiated business, the Business Model Canvas for quickly exploring and validating new business models, and serious games like Innovation Games for brainstorming new business ideas, and shaping and prioritizing requirements.


If there is one Commandment that is broken more often than not, it’s follow-through. Nothing deflates the team like inaction and ambiguity following your strategy session. Every strategy session should conclude with the following (so make sure you leave time for this – at least 2-3 hours!):

  • a plan for next steps and a summary of the key initiatives, including who is responsible for what
  • an outline of how progress will be measured and followed up on – how you will keep each other accountable
  • a check-in from everyone about what they’ve heard, and what they are personally committing to

Your planning sessions are one of the most important things your product team, or executive team, does during the year – so treat them that way. Like they always say – if you don’t know where you’re going, any road will do.

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