Is Your Team Stuck in the Past?

I’ve been thinking a lot about the past.

Not the past as in history lessons, but the past as in the unique experiences that each of us have, which inform and influence how we think and act today. Especially as business leaders. I wanted to grapple with how the past impacts the prospects of our future, because I’m hopeful that if we can understand it better, we can manage it better.

Most people see the past as a negative thing.

We’ve all read about that CEO doing something (or failing to do something) that seems utterly boneheaded from the outside. It probably is. It happens when something about the past created so much inertia, had so much gravity, wired itself so deeply, that things simply couldn’t have gone any other way. Strange, isn’t it? As humans we pride ourselves on being highly rational creatures, yet our conditioning from the past often forces us to act in highly irrational ways.

But if the past can have such a hold on us, can we do anything about it? Is it possible to take this same negative energy that pulls us backwards, and redirect it towards growth?

Terrified

For most of my life, the idea of being in sales terrified me. Sales, as I understood it, was something for the highly charismatic. For a special breed of people who possessed mage-like abilities to persuade, cajole, and woo. Definitely not me. I didn’t create that belief from some traumatic sales experience, though. It was just this general idea I had slowly formed through movies, TV, and culture. But seeing sales as something for “other people” held me back for a long time. It was a big reason I hesitated to go into consulting for myself. How could I survive if all my income relied on my ability to “sell?” The past had defined what I thought I was capable of, even though I was making conclusions based on osmosis, not direct experience.

But it turns out my situation is quite common. Because every client I’ve worked with has dealt with something similar.

For example, a brand I’ve been working with had, for years, been operating under the assumption that being “bold” would lead to bad things. There had been no crisis or PR blunder in the past. No trauma to shock the system into defense mode. It was just how everyone else in their industry operated, and that perspective had eventually become hardwired in the organization’s DNA. This “past” led them to a place where they looked and sounded like all of their competitors. They didn’t like being seen as a commodity, but they didn’t think that anything else was possible.

Or take early Intel. Decades ago, Intel was a highly successful provider of memory chips. It was “who they were.” They happened to make some microprocessors, but that was just a side business, subordinate to everything else. When the memory chip business became decimated (thanks to Japanese competitors who could undercut them on price) profits evaporated. But despite the red ink, Intel still thought of itself as a memory chip company. While Intel eventually forced itself to see reality and move into microprocessors, it only happened through some serious handwringing.

You don’t have to look far to see this happening now, though.

Consider SaaS. Every SaaS business has operated under the assumption that seat-based, subscription-based pricing is just how you’re supposed to operate. Some have even relied with this model for decades. Yet, even as “software” is being redefined to mean something else entirely (thanks to AI), and the legacy pricing model may no longer be tenable, there will be a huge swath of SaaS businesses who simply cannot adapt, despite knowing that their existence depends on it.

Sometimes we let the past put such a strong grip on us that we’re frozen.

I’m guessing you’ve experienced this personally. As a leader in your business, there’s something you know you should do, but can’t. You know it makes sense. You know that there will be negative consequences if you don’t. Yet the decision still sits there, unmade, like some apparition that keeps haunting you.

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Dual Polarity

But negative conditioning from the past doesn’t explain the full picture. The past has a dual polarity.

It can cast a negative light on your perspective, or a positive one.

Here’s the other thing I didn’t tell you about my sales journey. The first major deal I pursued, I won. And no, it wasn’t an inbound lead from someone ready to buy. It was cold outreach. That client went on to be worth multiple six figures. I would be lying if I didn’t say that winning that deal felt pretty damn good. But here’s what mattered more: that positive experience of winning the deal is just as much in my “past” as was all the negative conditioning about “not being a salesperson.” Half of my experience with sales was conditioned through a negative polarity (”I’m not capable of that.”). The other half was conditioned through a positive polarity (”I am capable of that.”) Where I ended up mattered more than where I started.

Think about what would happen if prior conditioning had no effect on us.

If that were true, we would never achieve anything worthwhile. Why? Because positive conditioning is what helps us push through adversity. I haven’t won every single deal since that first one. I have lost many. But because the past conditioned me to believe that I’m capable of closing big deals, I don’t get very frustrated when they go sideways. It’s simply something that has happened, not a reflection of my abilities or what will recur in the future. But without that positive bias I gained from past experiences, I might give up too soon. Or I might fail to put in the necessary effort to prep for sales calls, simply because I didn’t think success was even possible in the first place. What would be the point?

The Past Is Not Something That “Happens” to Your Business

The past can have a positive or negative polarity, but is there more to it? There’s another aspect to the past that most people overlook altogether.

The past isn’t something that happens to us. It’s something we create (maybe not all of it, but enough of it). And because we create it, we have control over it.

I love to mountain bike. Part of my hobby includes going to the downhill bike park, which is essentially a ski resort converted to a series of bike trails for use in the summer. These trails come with hazards: massive jumps, with big gaps between the takeoff and landing. Come up short of the landing and you’ll crash into the backside. Go too far, and you’ll land on a flat stretch, which usually ends badly. Lose control at any point while you’re in the air and it’s also ugly. All of these things have happened to me, on multiple occasions (I can show you the scars.) But the first thing I do after a crash is go off another jump as soon as possible. I know, it sounds unwise. But the reason I do it is to re-condition my perspective of jumping from a negative to a positive polarity as soon as possible. If I let a crash dwell in my head for too long, it will start to take hold of my confidence. Better to “flip” that polarity while I still can. Otherwise, I’d probably be too scared to try again.

I don’t see why business is any different.

Whatever you’ve been experiencing as a negative polarity can also be flipped. Maybe not in a single go. But what you can do is start to change that charge by degrees. You can do one thing that counters the negative perspective you’ve developed, and use that as a positive reinforcement signal to try it again. Maybe with slightly higher stakes.

For that brand that can’t see itself as “bold,” going for a complete identity change all at once would likely be too much, too soon. But what they can do is “try out” that bolder stance in a low-consequence way, maybe in a blog post or in ad copy that just a few people will see. If the world doesn’t explode, then hey, that’s positive feedback to keep pushing. Before long, they will have reconditioned themselves from seeing bold as “impossible and undesirable” to “who are we, and proud of it.”

Intel did this exact thing, actually. They wound down the memory business, by degrees, over the years, eventually devoting themselves entirely to microprocessors. Hard, but possible.

Avoiding Stasis

So now that we can see our propensity to be conditioned by the past for what it is (a survival mechanism, not a character flaw), we can treat it with more objectivity.

The same force that creates inertia is the same one that pushes us through difficult periods, just in reverse. Without that force, your life, and your business, would be static.

If your business is being held back by the past today, the only reason is because you are letting it. Since you can actively create “new pasts,” you can change the polarity of your team’s experience from something that pins you down to momentum that carries you forward. This isn’t just possible, it’s your responsibility. Because how else will things change?

Sometimes I wish we operated differently.

It’s heart wrenching to see a client know they should take action, but wrestle with the decision for longer than they should, stress out, lose sleep over it, and frustrate their team, before finally making the call. It’s hard for me personally, too. Often there are times I can see what I need to do for my own business, but I’m hamstrung by beliefs that have little to do with reality.

But I’m trying to look at things differently. I hope you can, too.

Whether your past keeps you from stepping forward or provides the very momentum you need to do something bold, depends only on how you treat it.

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As the founder of Flag & Frontier, John Rougeux partners with executive teams to align on their strategic narrative, build belief in the market, and win the next chapter of their business. You can connect with John on LinkedIn.