winning
Playing to Win, versus Playing Not to Lose
Life is funny. There are always ways to justify nearly anything you want (or don’t want) to do. For example, “The timing is not right” (“We’re not ready,” “The market will be better soon,” “We need to save more,” “We need to staff up first,” etc.) Justifications often include things like “We had a bad experience once” or “We are a very conservative organization” – comments that tend to lean towards risk aversion or a lack of confidence.

I’ve seen this in my own business after a large investment failed to yield the desired results, when I was a regional sales and services leader at a “growth-oriented” software company, and as a consultant. The root cause always varies, but the net effect is that those companies play it safe.
Why is that a problem? It may not be. Being content may not be a bad thing. Sometimes the status quo is enough. Having a reliable schedule, manageable stress levels, sufficient funds, and doing something you like with people you like may be the goal. But not everyone is built that way.
Growth usually means stepping out of your comfort zone, taking on risk, recognizing the need to adapt to stay ahead of the curve, and being OK with uncertainty. It means bringing on people with different backgrounds, skill sets, and perspectives than yourself. It can be very hard – especially if you are used to being in control and having the answers.
For me, the solution was twofold.
- We had to accept failure as an inevitable outcome. I believe this is where a lot of people stop. If you view failure as negative, then everything that stems from it (loss of money, a hit to your ego, and other setbacks) becomes your focal point. Lesson Learned: When you view it as a learning and self-improvement opportunity (“cognitive reframing”), it just becomes part of the cost of getting better.
From your team’s perspective, if everyone is as focused on the journey as you are on the outcome, people tend to view challenges logically rather than emotionally (thereby controlling fear). Success truly is a mental game. - We developed a structured approach for future investments (read more about it here). We treated each new venture like a project. It was focused, analytical, and unemotional. With this approach, speculative investments became easier each time. It’s amazing how that distance also helps switch the focus from risk to reward.
This understanding led to a presentation I gave that helped relaunch a company, helped several clients critically assess the risks and rewards of their plans, and may help someone consider whether they are focused on winning or simply on not losing.
As Richard Branson wrote in his book, Screw It, Let’s Do It: Lessons in Life, “If you opt for a safe life, you will never know what it’s like to win.” So, are you ready to play to win?
Lessons Learned from GTM Consulting
For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that went wrong 18 months ago, so I needed something that would allow me to take care of her, stay sharp, earn money, and help companies grow. What I encountered was quite different from what I expected, so I thought I would pass it along.
Most of the work was with small to midsize companies, but the problems and needs mirrored what I have encountered at larger companies. The main difference is that large companies tend to look to software to address problems. In contrast, smaller companies often lack the budget for what they view as a solution that increases complexity.
Here are my Top 5 findings:
- GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
- An interesting aside is that the company is often really seeking sales optimization but believes it is doing things “well enough” today and therefore needs to focus on new offerings and revenue streams.
- New perspectives on past performance and failures are well received but more surprising than anticipated. This leads to a better understanding of needs, which builds consensus moving forward.
- Sales teams are sometimes pitted against one another, rather than working together to help everyone achieve more (Coopetition – “A rising tide lifts all boats.”)
- Sometimes the competing team isn’t sales, but support. The team wants to help the customer (which is great), but works outside its defined scope instead of bringing in the services and sales teams to work jointly to solve the customer’s problem.
- Sales teams are focused on selling features rather than solving business problems.
- Training those teams on solution selling and understanding the prospect’s needs pays off.
- CRMs are not consistently used and often reflect idealized fiction rather than reality.
- Old, dead, or unqualified opportunities; lack of recent contact or interaction; deals that have slipped more than once; and a lack of understanding (company, needs, players, business environment) all point to an unrealistic pipeline.
- Sales management and teams are not leveraging AI to help focus their efforts.
- Conversely, they may view AI as a panacea, investing time and money in tools that supplement a strong team rather than focusing on strengthening the team.
Here are the related Lessons Learned:
- Selling is a byproduct of problem-solving. You can’t solve problems if you don’t know what they are. Every interaction with a prospect should focus on gathering information, building trust and relationships, and leveraging prior interactions to demonstrate that your solution will solve their problem and ease their pain.
- Here’s solution sales again. Teaching teams to ask better questions, listen more, and validate their understanding increases their standing with prospects.
- Identifying common business problems and describing how your product or service solves them should be the foundation of the plan.
- Perform market analysis. How do other companies describe those problems? Their terminology, often found in job postings by competitors and your target audience, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking and the problems they are likely dealing with.
- Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to both wins and ongoing customer growth.
- Paying sales teams for net new business only causes them to ignore install base expansion opportunities. And, if another vendor solves their problems, it is only a matter of time before they replace you.
- For one company, I convinced them to implement a 2% SPIV (like a SPIFF, but team-focused) for every team member who actively contributed to team improvement. SPIV payments were quarterly, and there was a running total so the team could see the fund growth. Initial indications of a positive impact are good.
- Another benefit of collaboration is that it helps teams focus on approaches that work due to ongoing testing and refinement. Collaboration also helps teams focus on a more accurate ICP (ideal customer profile). Sales management can then feed their findings back to Marketing to tailor and fine-tune their efforts.
- CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps.
- Using MEDPICC as a foundation for qualification is a much better start.
- Sales managers need to validate the information independently to ensure their teams are upfront and honest. Trust, coaching, and collaboration work together for the win.
- Chasing deals that are unlikely to close wastes valuable resources.
- AI is not a panacea, but it is very effective for research, market validation, prospecting, and meeting preparation.
- Going in prepared builds respect and credibility, saves time, and helps you quickly qualify prospects in or out.
- There may be opportunities to nurture prospects who have potential but aren’t qualified for immediate deals, seeding the pipeline for future opportunities. This could be a great place to leverage AI for personalized journeys with highly relevant curated content.
So, what are your thoughts? Have you seen some of these problems yourself? How did you handle them? Let me know in the comments below.
And if you are looking for assistance with your business, contact me.
Success is a Mental Game
This assertion is as true in business as in sports, individually and in teams. So, let’s break it down.

When I watch my local football team, I occasionally see a shift in facial expressions from excitement to frustration – often right before the end of the first half. Sometimes, they recover during halftime and come out renewed and ready to win, but the “gloom and doom” expressions usually translate into suboptimal performance and mistakes. It is frustrating because you know they have the talent to win.
The same thing happens in business – especially in Sales. Sometimes it occurs in the middle of a sales cycle, similar to the example above. Unfortunately, too many people allow a few data points to determine their future trajectory. Why is that?
Whether you own a company or manage a group of people, good leaders aim to optimize their workforce by balancing factors that lead to happy, loyal employees doing their best for themselves, their customers, and their company. Many motivational theories exist, such as Expectancy Theory, Reinforcement Theory, the Role of Instrumentality, Intrinsic vs. Extrinsic Motivation, and more. Since one size rarely fits all, the challenge becomes reward-focused personalization, which can be a lot of work.
People will often win or lose before they even start. Their negativity, self-doubt, and anticipation of failure become a self-fulfilling prophecy. This post focuses on self-motivation, attitude, mindset, and creating the habits that lead to better success.
Below are four simple questions that someone should ask themselves when they question their ability to succeed in a position, company, or industry. There are always many ways to point the finger of blame elsewhere, but the first step should be to look in the mirror.
- Do you believe that you can win where you are today? If not, why are you still there? Customers and prospects can sense insincerity, so if you don’t believe in yourself, you shouldn’t expect them to believe in you. Maybe the company is terrible, and everyone is failing. If that is true, then it is probably time to look elsewhere.
- What have you learned from past successes and failures, and how have you adapted based on those lessons learned?
- What are some early indicators of success or failure that you have identified? Are you adapting to the situation if you run into those indicators now? The best approach may be to cut your losses on this attempt and move to the next sooner rather than later (i.e., qualify out quickly).
- What are you doing to improve your skills? It is funny how small, continuous improvement efforts lead to a greater sense of confidence. Greater confidence often translates to increased success.
I have found that consistently doing the right things is the best way to maximize my success. Start developing habits and routines that have led to winning in the past, but don’t expect them to work forever. Everything changes, and you should change, too. Look for what’s working for others, try it out, and if it works, incorporate it into your routines.
Success truly is a mental game, and everyone can win. The person who keeps winning over time is the one who doesn’t get stuck in time. Be curious, get excited, and adapt. And once you get there, start helping others. Having mentors is nice, but it is also great to become one.
As the saying goes, the rising tide lifts all boats. Winning can be a team sport, but it begins with individual contributors having winning attitudes. Unfortunately, the same is true of losing, so decide now what you want and move forward with energy and confidence.
