Strategy conversations by their nature are difficult. After all, inherent in solving the strategy problem for every organization is the need for honest, frank assessment of the situation. In my experience, honest and frank are often critical missing ingredients in these challenging discussions, replaced by politics and posturing.

Effective leaders and managers learn how to cut through the fog of noise and politics to run conversations that ultimately lead to a clear understanding of the real challenge(s) confronting their business.

Strategy War Stories

I wish I had happy stories to tell about strategy work. Mostly, they’re war stories.

In my corporate life, going from “You are here” to “Here’s where we’re going and how” with strategy work, ranged from months to years. Much of this time was filled with consultants bearing magical templates that proved not to be too magical and executives engaged in an almost endless set of silo wars. It’s amazing what lengths people will go to in pursuit of securing their current real estate or positioning themselves for fresh conquests in a new strategy situation.

In one organization facing a slowly evolving existential challenge, it took two years of executive flailing to pull it together and face reality. It also took the horrendous shock of 9/11 to melt the resistance and summon the courage to tackle the issues head-on. Throwing a few of the toxic political actors off the bus likely allowed the right kind of dialog to emerge.

In more than a few wandering organizations, I observed the absence of strategy ultimately manifest in these wanderers being co-opted into someone else’s bigger strategy. While not particularly bad outcomes as it turned out, running on auto-pilot hoping for someone to rescue you from the vagaries of the market forces is at best a horrible strategy.

Why the Strategy Dialog Goes Sideways

The work of diagnosing an organization’s situation—effectively assessing, “We are here, and this is what it means” involves surfacing failing initiatives and approaches as well as confronting limitations in the face of changing external factors. Since we are mostly wired as humans to survive and maintain a steady-state environment, talk of limitations and misfires is fighting our nature. Add organizational politics and the Game of Thrones environment that exists inside many firms, and it’s no surprise this is difficult. Nonetheless, survival and the pursuit of success demand we move beyond these human frailties.

5 Keys to Improving the Effectiveness of Strategy Discussions

While I suspect I’ve painted a mostly dark side of human nature when it comes to strategy, I’ve been around as a contributor or guide when it has worked, and the experience was transformational for the players and organizations. Correlation is never proof of cause, yet there are some stark similarities across those environments where the strategy dialog turned honest, productive, and ultimately, valuable for the organizations.

1. The CEO Must Be Committed to Cutting Through the Noise

If the top job wasn’t challenging enough, the organization’s senior leader must be aware of the inherent challenges surrounding strategy discussions and work unceasingly to navigate those challenges.

Expectation setting and even calling out the requirement for clarity and honesty in the form of strategy team values are potent approaches. Crying foul on any deviations from the stated or implied values for transparency and honesty is essential. And of course, adhering to those values with their behavior as potentially mistaken CEO decisions are identified or require reversal is core to success.

2. Strive for Beginner’s Mind Thinking and Ask for Outside Help

The natural tendency of most strategic initiatives is to rubber-stamp the status quo and perhaps propose incremental changes to what’s been working. You can get away with this—particularly in a growing market—until something shocks the system.

Once the shock is present, your biggest adversary may well be the experience and dominant logic you and your team members bring to the situation. After all, our brains are fantastic pattern matching machines, and your pattern matching is a function of your prior experiences. Of course, in an existential threat to the business, it’s imperative to clear the cache and rethink everything.

The Beginner’s Mind concept is powerful for these circumstances where what used to work no longer hunts. Effectively placing your collective experiences on a shelf and looking at a situation through fresh ideas opens up new lines of thinking and dialog. Of course, it’s darned hard to do, so consider adding in objective outside individuals who don’t have the same base of industry, customer, and business experience as the core team members do.

3. Adopt A Parallel Process for Talking (and Arguing)

The single most empowering process for guiding group discussions in tough situations I’ve encountered is Edward De Bono’s Six Thinking Hats approach. I’m relentless in preaching the value of parallel thinking and guided parallel group discussion enabled by his technique. Either engage someone experienced in the process to help the team move through the robust discussions, or plunk down the less than $20 for the book, invest a few hours and then practice the technique.

The beauty of this parallel talking process is in its simplicity! If I’m on a deserted island with eight members of a management team who need to figure out how to survive and ultimately get rescued, you bet I’m drawing on De Bono’s approach!

4. Have a Game Plan for Decision-Making

Ultimately, a strategy is about making decisions on what to do and importantly, what not to do. Some teams run into a brick wall here—sometimes at a high rate of speed, and their inability to break through and make tough decisions creates catastrophic damage. Teams that either make it through, over or under the wall, understand the importance of decision-making and they apply the process with rigor.

Some key questions successful strategy teams ask and answer, include:

  • What’s the real problem we are solving?
  • How will we decide?
  • What do we know?
  • What do we need to know to make this decision?

And they spare no expense in asking outside help to evaluate and challenge their assumptions. And while it would be nice to think that ultimately strategy dilemmas reduce to some data-backed decision choices, most of the time, there’s a serious leap of faith essential for the decision.

5. Accept that You Will Need to Summon Courage in the Face of Ambiguity

A few years ago I led a strategic initiative focused on recasting an old firm in a new market. We navigated all of the above headaches but persevered. Ultimately, we identified an almost serendipitous convergence of market forces and opportunities in front of us. Even better, our core abilities neatly translated into this world, albeit with some investment and infusion of new talent.

After achieving the board’s strategy team lead’s approval (a former McKinsey senior partner), I needed the CEO to agree to let me send the final strategy packet to the entire board. He held the FedEx package in his hands and began questioning everything about what we had concluded. Since he has sadly passed away, I will leave the real dialog to the memories of the three of us present at the moment. Suffice it to say it was terse. He relented, we shipped it, gained the board’s support, and more importantly, we brought a firm to life and market leadership building on it.

You’ll face your massive moment(s) of doubt when it comes to making the big calls essential to either survival or success. There are always risks, and there are never clear views to the future outcomes. You will need to summon individual and team courage to get in the game. Easy words but watch out for the sleepless nights.

The Bottom-Line for Now:

We march through our lives and careers one challenging conversation at a time. For organizational leaders, the challenging discussions of strategy are among the most difficult. Accept and embrace them, and fight through these conversations with honesty, passion, and a willingness to learn and grow. It’s the only way forward.

Art's Signature