Adapting To Today’s Realities, A Ruthless Pragmatist’s Guide

For the past several weeks, I’ve been writing some fairly esoteric/philosophical things. Talking about entanglement, durable revenue, rethinking value, and that value is in the friction. But most of you know me as a “ruthless pragmatist.” You are probably confused–and you should be.

So I’m embarking on a series of articles, moving from philosophy to practice, theory to execution. My hope is to help you think about how you can take these abstract concepts and actually put them into practice. Let’s start with our GTM strategies.

First, we need to stop pretending our GTM strategies are working they way they are diagrammed on paper or the screen, that they are working the way we want them to. They’re not!

Our pipeline coverage is bloated, our outreach isn’t reaching, buying cycles are unpredictable, win rates declining, engagement (employee and customer) is plummeting, expenses are sky rocketing—and we have AI, the cure to all our worries.

We continue building plans as if the world, our customers, our people are playing by rules we wrote five years ago.

The reality is everything has shifted, profoundly. And it’s continuing to shift. As a Californian, I’ve been in rolling earthquakes. It’s not sudden jarring, it’s the rolling, the up and down that continues. The ground is shifting an we try to maintain our balance. So we have to reset.

I’m not suggesting we abandon our models, processes, methodologies, systems, and tools. They still serve us. They aren’t the problem, it’s how we use them. We have to change our thinking, we have to ditch the ideal and deal with the real!

Our ICPs, buyer journeys, pipelines, bow-tie models give us a sense of order. But they are built for a world that doesn’t exist. Buyers and buying isn’t linear. It’s messy. It starts and stops, it shifts and changes. Buyers ghost us, some leave the process, some come in mid process, they constantly loop.

We have to deal with that messiness, that constant shifting. We have to train our people to adapt and adjust to the customer and the situation. While our processes serve as a guide, they have to adapt to the reality of the situation.

We design our strategies for control and predictability, but we have to shift to design for reality. I’ve written about the messiness and the friction, but that’s the world our customers and our people live in. So how do we engage them where they are at?

Our customers aren’t buying solutions, they are solving problems. Problems they don’t understand. Being customer focused isn’t about being responsive and solving problems. It’s about becoming embedded in their thinking and how they operate. We have to move our customer experience thinking from do they like us, are they realizing the value, to “what would happen if we disappeared?” If our absence isn’t noticed, if the hole we leave is easily filled, then we are vendors, not partners.

We have to show up to our customers differently. It’s real conversations, collaborative problem solving, friction, pushback. It’s in these real conversations that we drive engagement, trust, and create meaning.

We have to stop skipping over the fundamentals, the basics. What breaks in our GTM execution isn’t our strategies, diagrams, goals, it’s the absence of clarity and purpose. We over complicate our messaging. We rush to solution, demo, close, without confirming the buyers agree within themselves about the problem and the need to change.

We need to constantly be revisiting our strategies, processes, methodologies, metrics, assumptions. We need to ask hard questions like, “What has changed? Where are we losing the connection with our customers and our people? What assumptions have we made, but no longer hold up?”

We need to think–critically! We need to train our people to think and empower them to figure things out. It’s not about following the steps, but the ability to sit back and think, “What’s really going on?” We need to create the space to adapt and exercise judgment. We need to coach them not on compliance and metrics, but in how to engage with meaning and purpose. We need to recognize this friction in our coaching discussions is where the real value comes.

We need not to lecture about accountability and metrics. We need to build teams confident enough to tell the truth about what’s really happening, and coach them in developing the agility to change. It’s not about command, control, dashboards. It’s from a culture that rewards curiosity, learning, problem solving, and ambition. It’s about rewarding the ability to push through.

The world, our customers, our people are moving on. We have to move with them, we have to provide the leadership to inspire our people, customers, and ourselves. Imagining new possibilities and the simultaneous challenge and excitement of pursuing them.

So as a ruthless pragmatist. Some simple ideas:

1. Reality check your process. Look at 5-10 recent wins/losses/no-decisions. Map how they actually unfolded versus how our models wanted them to unfold. What do we need to adjust, what do we need to change, how do we adapt?
2. Ask the “so what” question. If we were to disappear in the buyers buying process, would they notice, would they care? If we were to disappear in our current customers, would they notice, would they care, or would they find a replacement? If the answer is “No,” then we aren’t creating the value meaningful for them. We can never become entangled with them.
3. Reframe every conversation. Stop pitching! Start discovering, learning, collaborating. Start dealing with the messy worlds our customers and people live in. Learn, adjust, adapt, move forward.
4. Use the friction as a tool. Friction reveals misunderstanding, disagreement, assumptions, judgment. Don’t avoid the friction, it’s in the friction we get things done.
5. Simplify–ruthlessly! Strip things down to the basics. It’s not about all the models, dashboards, metrics, tools. It’s not about the long lists of all our capabilities. It’s about our checklists, it’s about what’s most important and impactful right now and how we move forward.
6. It will never be perfect. And it will never be! Don’t obsess over the neatness and clarity of your bow-ties, the checklists, the playbooks, the metrics. Roll up your sleeves and dig into the mess. That’s where the work gets done.

I’ll stop here. Over the next couple of weeks, I hope to dive deeper into this wonderful messiness of getting things done. I’ll be carving off different views–still rooted in the philosophical thinking I’ve done over the past few weeks, but ruthlessly focused on execution. Enjoy the ride, looking forward to your engagement.

Afterword: This is an inspiring AI generated discussion of this post.  I’m fascinated how they take my ideas and simplify them further!  Enjoy!