success

Repeatable Sales Motions vs. Individual Selling Success

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A sales organization that consistently exceeds aggressive goals is the holy grail for growth-focused companies. A repeatable sales motion is often seen as the vehicle to make that happen. Unfortunately, few companies have translated salesmanship and the art of selling into the science of repeatable sales.

Often, one or two successful deals become the foundation for what is believed to be the repeatable sales motion. Two common scenarios are:

  1. You may have lookalike prospects to target based on a limited sample of sales. That doesn’t mean there is real scale potential, but it is a start.
    • This approach fails to address other independent variables, and often results in an approach that is neither repeatable nor scalable.
  2. You have one salesperson who is very successful, but their success has not been repeatable.
    • The nice thing about this scenario is that a repeatable sales motion is more likely, but understanding the subtleties of their approach can be difficult to quantify, document, and turn into something repeatable.

Let’s take a more analytical look at what works and why, which leads to a better understanding of how to develop repeatability.

As the Roman philosopher Seneca is quoted as saying, “Luck is what happens when preparation meets opportunity.”

Preparation is more than understanding the prospect company, their competition and differences, the market they operate in, and what changes may be coming (technological, legislative, economic, etc.)—although that is often far more preparation than many Account Execs bring to a meeting. I’m always amazed at how unprepared many sellers are, and that is the quickest way to lose your prospect’s respect.

I’ve learned over the years that planning for the unexpected is planning for sustainable success. That can be as tough and nebulous as it sounds. You need to stay calm, unemotional, and in control while assessing the situation and adapting on the fly. Confidence definitely helps, as does logic. Composure is key to presenting a professional presence.

I like the Five Whys method of drilling into those statements or concerns to understand them. Sometimes it’s fluff, but often it helps you close the deal faster because you uncovered a pain that others missed. This can also help qualify a prospect out quickly and move on to a better fit that develops into a closed-won deal.

Salesmanship includes:

  • Being prepared.
  • Being friendly, approachable, and likable.
  • Relationship building. It starts with finding connections and common interests, then demonstrating your ability to help the prospect solve their problem (and at this stage they may be more focused on symptoms than root causes).
  • Understanding the need. Why is this important to them? Document this, including their phrases and terminology, as that can have a huge impact on their acceptance of your proposed solution.
  • Having value to add. This includes product knowledge, company knowledge (website, 10-K/10-Q, articles, etc.), competitive knowledge, industry knowledge, and more.
    • This gives you a perspective on their business that may not be 100% accurate, but it lets you make assertions the prospect will likely validate or correct. Your knowledge will also impress them and likely lead to deeper discussions about their needs and goals.
      • AI can significantly reduce your preparation time for this.
  • Being respectful. This starts with respecting their time.
    • Don’t be late to calls. Don’t spend time on things that are not relevant. Don’t ignore the people that you are speaking with by focusing on higher-level decision makers. And don’t badmouth other products they may be using or competitive solutions.
  • Being focused on solving their problems. Without this, you won’t build a loyal, lasting customer base.
    • To me, this is as much about reputation as it is about salesmanship.
  • Learning from failures (yours and others) as much as success. Evolution matters: improve and become your best.

These are all teachable/learnable skills. They also address the intangibles that fuel selling success.

So, which came first – the selling successes or the repeatable sales motions?

To me, they go hand-in-hand. By building a high-performance sales team, pooling information from sales discovery calls and other meetings, and focusing on patterns of unmet needs and the associated messaging, you can create and refine something repeatable. It takes more than one or two wins to prove a pattern exists, so create a hypothesis early and work to refine or refute it with every prospect interaction.

Selling may not come naturally to a lot of people (it wasn’t for me), but it is a muscle you can develop with hard work, practice, and a goal of improving every day. Your success may look like luck to others, but you will know better.

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Playing to Win, versus Playing Not to Lose

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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?

This entry was posted in Business Ownership and Management, Change Management, Consulting, innovation, leadership, strategy and tagged , , , , , , , , , , .

Is Your Sales Team Killing Deals in the First 30 Seconds?

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How many times has a stranger called you or filled your inbox with a message that starts with their name and a generic company intro? Did it make you want to pay attention, or did you immediately hit “delete”?

An image of a man in a suit, reaching out with his right hand to point to a graph with an upward trajectory.

For executives overseeing high-stakes enterprise sales, this isn’t just an annoyance—it’s a performance barrier. If your team is stuck in a “Me and We” mentality, they are burning valuable leads before discovery even begins.

The Problem: You Can’t Win if You Don’t Get to Play

Most sales and marketing teams default to talking about themselves. They lead with their history and their product features. In enterprise sales, this is a fatal error.

Unless you are a dominant market leader, your prospects don’t care who you are or where you work; they care what you can do for them. Every second spent on your “About Us” slide is a second lost in identifying the prospect’s pain points.

The Cost of Misaligned Messaging

When your team uses “me-focused” messaging, the consequences are immediate:

·       Low Engagement: Cold calls and emails are ignored because they lack immediate relevance.

·       Stalled Demos: Prospects tune out during the “logo slide,” reducing the probability of real engagement and follow-on from this point on.

·       Failed Discovery: Without quickly developing rapport and a focus on the prospect’s specific business and terminology, your team will never uncover the deep-seated issues required to close a complex deal.

The Solution: Use a “Prospect-First” Framework

To fix your pipeline performance, your team needs to pivot to a PIE-based approach that leverages your perspectives, insights, and expertise to prioritize the prospect’s desired outcomes.  Help them visualize that better outcome, using their terminology and scenarios, with your solution.

1. Establish Immediate Rapport

Before the call, find a “hook”—a shared hobby, a mutual connection, or a specific business challenge they’ve mentioned in forums or job postings. Connection builds the rapport necessary for a successful discovery.

2. Lead with PIE (Perspective, Insight, Experience)

Instead of introducing your company, lead with the problems you solve. Help them answer the “why you?” question by demonstrating expertise and a proven solution.

·       The Shift: Instead of saying “We are the leading Kubernetes platform,” try: “About half of the executives I meet are concerned about unplanned outages, spiraling costs, and security exposure. Have these been concerns for you?”

·       The Result: This adds instant credibility without making the conversation about you. It forces the prospect to engage with their own problems if they are truly interested in finding a solution. If not, you both agree there is no fit right now and move on.

3. Skip the Ego, Show the Success

In your next demo, skip the logo page and the multiple feature pages. Move directly to a relevant customer case study from a similar industry. Discuss their specific issues and the measurable outcomes that must be achieved. This makes your solution relatable and positions your team as experts who can help, rather than just another vendor. Build rapport and earn that next meeting.

Audit your team’s outreach today. Are they leading with “We” or with “You”? If your messaging needs a strategic overhaul to better reach your future customers, contact me here. Let’s turn your sales messaging into a competitive advantage.

How is your team changing its approach to meet today’s better-informed yet more skeptical enterprise buyers? Let me know in the comments below.

This entry was posted in Business Ownership and Management, Career, leadership, Selling and tagged , , , , , , , , .

Lessons Learned from GTM Consulting

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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.

A generated image of a male consultant working with a sales team.

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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.

This entry was posted in Artificial Intelligence, Business Intelligence, Business Ownership and Management, Career, leadership, Selling, strategy, Technology and tagged , , , , , , , , , , , , , , , , , , , , .

Sales Discussions that Work

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Selling is challenging work, and often, “we” (sales and marketing teams) make it even harder than it needs to be. How many times have you seen a selling script, elevator pitch, or initial presentation that is long, boring, and undifferentiated? People have short attention spans, and nobody wants to interact with someone who doesn’t listen or is pushy.

Photo by fauxels on Pexels.com

Your initial discussion is crucial to your success. Instead of going over a list of features, reading a slide deck, and telling why you and your product are so great, let’s try something different.

1. Understand why people buy. Any change can be difficult, risky, and painful. So, the pain they are facing has to be even greater than the potential pain of change, or they won’t bother changing.

Your main job early on is to listen and work to understand their concerns. You may have a perfect solution, but if it doesn’t solve their pain, it holds little value to your prospect. This initial meeting is all about them.

2. At the start of the meeting, ask, “What would make this time well spent for you? What would you like to walk away from this meeting with?” Get them thinking about their problems and the value you may be able to provide, even if they don’t fully articulate them to you.

3. Ask questions and follow-up questions. People don’t lead with their significant issues, and someone unwilling to divulge anything likely isn’t a buyer. The more the prospect talks, the more you learn. So many sellers do not understand this simple concept. They want to dazzle you with features and demos – even if those things are not what the prospect needs.

4. Once you think that you have identified a pain, restate it, qualify and quantify it. For example, “You mentioned that your product release cycles are too long and complex. What is the business impact of that, and what would the impact be if you could reduce that time and effort by 50%?” Write their response down, in their own words, because it could be vital later.

If you identify several pain points, review them and ask the prospect to identify the top three issues from the list, and then ask why those three. Once you have their answer, ask if other stakeholders in their organization would agree with that list, and why or why not. Again, get them to expand their thinking and work through this, as it will help you identify other stakeholders who may have other priorities.

5. If you are giving a presentation, pull up the most relevant slide (customer problem/benefit slides work well here) and ask if this sounds similar to the problem they are facing. It can be a good starting point for getting the discussion moving in the right direction. By providing relevant information, especially about how you solved a similar problem for another customer, they will see the value of providing you with more data and information.

6. Don’t worry if you are not able to cover everything you intended, as long as the meeting is productive. I’ve also seen salespeople cut someone off and move on to a new slide rather than discussing something of substance. I was actually told once by a sales leader that five minutes of discussion is all that is required in an initial 30-minute meeting, because our goal is to pique their interest. That approach just doesn’t work. You may impress them, but if you don’t start building confidence that you can help them, there probably won’t be a second call.

7. Next steps. Keep in mind that your time is valuable, and qualifying out a prospect who is not a good fit is essential – it helps you avoid false hopes and lets you focus on people who might genuinely need your help. The next meeting could go many ways, but it’s best to ask the prospect. Would they like to expand the audience? Is there a specific issue they would like to address? Would they like a product demo or a technical discussion? Is something like a non-disclosure agreement (NDA) keeping them from opening up? Lack of engagement on their part is a huge clue. Be direct and ask the tough questions now to avoid wasting valuable time and effort later.

Here is a mini success story. In 2010, my team and I began selling the first commercial vector high-performance analytics database. Several products were already out that claimed to be 70x-100x faster than others. Our pitch was that we were 70 times faster than other products. That was self-limiting from the start and likely prevented people from contacting us.

After two months of minimal success (I closed a deal with a small hedge fund, which was the only sale in all regions), we started a weekly webinar called “Why Fast Matters.” The focus was on positive business outcomes rather than specific technology and features (“speeds and feeds”). We opened with some “What if?” statements, such as: What if you get answers from complex queries faster than your competitors? What if you could do that without the cost, complexity, delays, and limitations of a Star Schema or pre-aggregated data? What if you could do this on commodity x86 hardware? We would then briefly cover the breakthrough technology (a precursor to Snowflake) and offer a free half-day meeting with a consultant.

Within the first two weeks, we met with a company that was later acquired by PayPal shortly before eBay acquired PayPal. This company was about to spend $500K on a proprietary hardware expansion that would have only provided additional capacity for the following year. Their customers bought advertising based on queries against the last six months of their data. I asked the question, “What if they could query against five years of data and get answers faster than they do today? Do you think that would help them buy more advertising? Do your customers ever ask for this?” They said their customers frequently ask for 12 months of data and would be willing to pay more for these capabilities. Still, they did not have a way to do this cost-effectively.

I closed a $360K ARR subscription deal in two weeks, and they purchased $100K of commodity Dell hardware for our software to run on. They saved 8% over their planned purchase, and more importantly, they rolled out advanced querying capabilities (against six years of data) in less than a month. There was incredible value to them and their customers, and it generated more business for them. We wouldn’t have identified this need if we’d focused primarily on features and technology.

As an aside, I was initially chastised for going off message, but after the Australian team adopted our approach and began closing deals, it became the new corporate standard. If something isn’t working, focus on finding ways to improve it. Even incremental change can be meaningful.

In the words of Tony Robbins, “If you do what you’ve always done, you’ll get what you’ve always gotten.”

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