Board Game Strategy for Sales and Business.


Board Game Strategy for Sales and Business.

Sales are mostly checkers, and everything else is chess.

My firstborn, my 10-year-old son, whom I love, just recently finished going 10-1 against me in chess.

In fairness, I’ve never played before he taught it to me in stress-free chess, or something like that.

In some fairness, he had a week head start playing for a week. (He was on spring break with some friends, and our friends thought it would be funny to teach my son to kick his father’s tail in chess.)


It’s humbling. And frustrating. He’s 10. I’m 41.

All my insecurities have been reinforced by this experience.

But I’m learning.

Thanks, Gamestop!


B2B Sales (is) Tactics.

Or at least a lot of it is. Most people reading this aren’t in long, complex enterprise sales. A few of you are. Most aren’t.

Most of us aren’t in anything approaching the complexity of Washington D.C. and the way agencies, lawmakers, and the press have to be coordinated.

THAT is somewhat similar to true, enterprise sales that involve multiple departments, dozens of meetings, legal, finance, engineers, and more. There, you will need to coordinate, anticipate responses from various parties, think through political alignments, how to head those off, where to pull strings, call in favors (on both sides), and more to get something done.

A Google search on B2B sales cycles says they take, on average, 4 months. That may be right, depending on where the starting point is.

Here’s the deal, though: most of this is small business selling to other small or mid-sized businesses (at least in terms of transaction volume). That’s often a few steps and stages to get from suspect to closed deal.

It’s largely about great first conversations and qualification (or discovery) meetings.

Checkers is great – you can think 1-2 steps ahead and set up the opportunity to convert.

And I’ve played a lot of checkers. Ask my son. I’ll smoke him in checkers.

And I can set up opportunities through effort, volume, and recognizing a few tactical opportunities to win business. So my checker’s talent rolls over.


Simple Sales Tactics

In my sales coaching program, I mostly work with small business owners, consultants, and professional service providers. Sometimes I’m working with debt or equity funds, or someone in commercial finance.

Shorter sales cycles.

We focus on a 4 stage sales process, and the moves necessary to advance most deals through.

What does this look like?

  • Core questioning strategies
  • The right order in which to ask questions
  • The right staging of questions and qualification
  • Handling the tough questions from prospects
  • Handling other decision-makers or players
  • Dealing with resistance from prospects

Once it’s burned into the muscle memory, it stays, sort of like riding a bike. It takes some time, but it can be applied across industries.

The Dirty Secret About B2B Sales

Do you know why it can be applied across industries? Because selling is largely the same. Yes, there are differences:

  • The titles and personalities of the people you’re selling to
  • Size of the deals
  • The products or services
  • Terms on the deal
  • Margin
  • Buying cycles and seasons

But the core qualification remains the same:

  • Finding someone with an issue, who wants to solve it
  • Finding a compelling reason to do something
  • Quantifying the impact of inaction, or upside
  • Uncovering if it’s a nice-to-have or need-to-have
  • Understanding if they’re doing something, or if inaction is an option
  • Knowing the buying process and criteria
  • Dealing with money and budget (or investment)
  • Identifying and talking with the key players

That’s it. Those are the move. There are sub moves in there, but once learned, it stays.

So what about chess?

Business and Career Strategy

So enter chess and my son smoked me repeatedly.

I used to coach high school football and spent all my time on the defensive side of the ball. We loved defenses focused on pressure and physical coverage. Part of is a personality disorder on my end: I’m a third-born, or I’m from the South, or my college team is perpetually struggling (Thanks, Tennessee Athletic Department), or something else.

Buddy Ryan’s Bears’ defense, the 46, was the epitome of pressure. Won the Windy City a Super Bowl.

Pressure and physicality are great in defense: it leads to confusion, turnovers, and negative plays.

It also leaves one exposed to the big play. And if the pressure isn’t systematic, thoughtful, and strategic – in short, if it’s emotional – it creates many big plays against a good play-caller.

Checkers doesn’t require as much self-control as chess.

Chess asks us to think at least 3 moves ahead. Often more.

Want examples? Here’s what I *should* be thinking about when playing my son:

  • His Rook can immediately take mine if I don’t move mine right away.
  • If I move my Rook, he’ll jump his to try to check my King.
  • That’ll force me to use my Rook or Queen to take him off the board. I should consider that.
  • If I move my Queen, am I exposed to his Bishop’s lateral move?
  • If I am exposed, whom do I want to lose first, the Rook or the Queen?

That’s one line of thinking, assuming I get the rules.

How does this apply to business in general? Or career?

I’m glad you asked.


Thanks, Gamesver!

Plotting Career Moves

If I were a younger man, and wiser, here’s how I’d think about career. (And apologies to every teacher and mentor whose advice I wasn’t patient enough to follow.)

  • I’d get really clear on what I wanted at 50. Seriously. I’d spend a year figuring this out. Interviews, observations, trips, whatever.
  • I’d begin plotting toward that and working backward. Let’s pretend I want to be a CEO for SomeGreatCompany. What role do I need to get there? CFO? VP of Finance? Head of Sales?
  • I’d continue working back. Let’s pretend I need to be a CFO. How do I get to CFO? What are the moves that need to happen? In what sorts of businesses?
  • I’d ask and try to answer, “Which is more important- tenure in a role/company, or experience by title?” That’d help me plot my course.
  • From there, I’d plot out moves and contingencies. For example, what if that other analyst moves up before me? What if that head of finance never leaves or retires? What are my moves then?
  • Based on the companies I’m looking at, I’d consider the strength of management, how they’re funded/capitalized, the key players in key departments, and their competitive position. You have to. Because if you don’t, you get in a company and realize, “Dadgummit. I forgot the Bishop.”

Look, I’m not great at the career thing. I have a few very profitable skills, but I have not placed enough emphasis on certain types of experience, titles, or duration in certain spots. I’m overly confident in a few skills, and I have a lot of faith the Good Lord will look out for me when I’m an idiot. So take this for what it’s worth.

But I have been in a lot of companies and can apply chess better there. Because every business is an opportunity, and every business has the opportunity in it.


Business Strategy and Chess

If considering investing in or joining a company, it’s important to understand what can take your King. And weigh all of those.

  • Where is the product? Is it adopted? What are its deficiencies? Do I really understand the risk associated?
  • How does this stack up with competitors? And where is their funding? And thus, their timeline to outflank us?

When I got into the insurance game years ago, I didn’t research the competitive situation well enough. Even if I had, it may not have stopped me from joining that firm, but I would’ve been better equipped to handle the uncertainty ahead.

  • What about the management team? Are they talented? Experienced in the right ways? Aligned? Staying? Do they have a healthy culture?
  • How is their funding/profitability/runway/capitalization? The unit economics and burn rate are important. Very.
  • Do they have the right board with the right oversight? Kind of important if they’re making decisions.
  • Are customers leaving? Reducing spend?
  • What macroeconomic factors exist that could impact us?
  • What assumptions am I making, that if I knew would change, would keep me from taking this role?

For instance, I jumped into commercial finance – non-bank lending – in early 2020. Again, checkers and the Knight of Uncle Sam took me off the board.

But what if you’re the operator? It’s your business, or you’re an executive and you aren’t going anywhere. Questions to ask about the players on the board.

  • What do we prioritize? Product, sales, or account management? Because we have to choose.
  • What if our conversion rates drop?
  • What if our competitor takes a portion of our resellers?
  • What if there’s a legislative change in a key market?

You have to play chess – know where the Knight is, how the Rooks and Bishops are positioned to pounce, and how to defend your key players (Rook, Bishop, and Queen) to defend your King. It’s multi-level thinking.

It involves sacrifices and tradeoffs and true prioritization: there can be only one.

And I’m just learning.

If it’s your career, you have to think like this.

If it’s your business, it’s more than your career; it’s also likely your net worth. You can’t afford to play mental checkers. Unless you’ve got a killer COO who does that for you. If that’s the case, go sell something. Profitably.

Till then, remember – live by the blitz, die by the blitz. And be willing to trade pawns for a royal court.



Adam Boyd