Stepping into a new sales enablement role is tough. Even if you’d had great successes in the past, one size certainly does not fit all.

I have a career spanning almost 20 years in sales and sales adjacent roles. In that time, I’ve made many hilarious and epic mistakes. I hope that in sharing them with you, you will be able to take the insights that I had to learn the hard way and adapt them to your own situations.

Because the amazing thing about messing up is that you learn amazingly well what not to do the next time.

The gist of the rest of this article is: picking and choosing battles, deeply understanding what your endgame should look like, then figuring out how to get it all to work.

Enablement is both a catalyst and a capstone

Why do I say this?

More likely you have come to this article because you have been thrust into a situation where you’ve been asked to ‘enable your audience’, with little oversight or guidance.

This is normally in response to some performance or data indicator that did or did not go according to plan.

Congratulations! you are not officially a part of the ‘I don’t care what happens now, just make sure it doesn’t happen again’ crew.

Previously, I’d say about 10 years ago, it used to be that we had to train them. Prior to that it was we have to do change management.

Historically, things tend to go cyclically and everybody’s looking for that silver bullet. And the bullet today is enablement.

Before we go to deep into the rabbit hole of enablement. I’d suggest that you clearly understand the difference between enablement and readiness as the two are often thought of interchangeably but are not the same.

In today’s modern world it's better to start out with clear definitions of what you are doing versus what you are not.

So, now that you’ve clarified what you are being tasked to do, the terrifying option of deciding what the first step is can sometimes be overwhelming.

Some might suggest that you start with training or you want to start with content, or you want to start with an idea.

Before you become overwhelmed with options, I want to clarify it’s all about starting with one activity and one outcome then and figuring out how to navigate to that next one.

So then what are each of the steps along the way?

This is one of my more glorious failures

As an illustrative example of where I tried to begin, I want to tell you a story.

I had an amazing opportunity to lead the enablement and training for the University of California for UCPath.

It was a training and enablement program that sought to centralize HR functions for economies of scale, rather than the disparate processes and systems that had proliferated across all 20 universities, laboratories, business schools, and law schools.

Specifically, I had to enable 200,000 University of California employees from their homegrown and deeply entrenched HR tools and processes to PeopleSoft.

For context, a good portion of California state taxes is spent in just managing HR paperwork through ~1200 different data systems.

Many of those systems don’t even talk to one another and are sometimes built with and on machinery and code that is no longer being supported. In addition to outdated tools, the coding languages they were built on is no longer taught in schools, or the programmers that built it are dying.

Yes, really.

This was just half of the challenge.

Not only that, because all 20 universities had their own thing going. Each university and sometimes every college had they own way of working, which they had ‘perfected.’

As the ‘cherry on top,’ every single university is non-hierarchical. There was little consistent structure that I could learn and then apply to other locations. The janitor had the exact same amount of say, as the comptroller, or the CFO.

From an enablement perspective, it could quickly become overwhelming. Like attempting to eat an elephant with a spoon in the dark.

Where did I start?

I started with the people.

Because this change was happening to individuals, not for them, not around them, it was happening to them.

And in recognizing that it happened to them, all of the other aspects that come along with this transition, I had to structure my plans with people at the center.

Everything else about the project had to orbit the people, and so it made the most sense to focus on the audience first.

These other people changes, the process changes, or even the product that we were introducing didn’t really matter unless I had a very clear understanding about why they should care about these other satellites to their own worlds.

My spectacular failure was this: culture eats strategy for breakfast.

Although I had correctly identified that people were at the center of this technological transition, I approached this in completely the wrong way.

I approached this like an industrial rollout. And I used classical organizational change management processes, which are very clearly aligned to the 1940s, 1950s, 1960s, and are all about the top-down, command-and-control organizational structures, and I got taken to task.

My initial attempts were complete failures because I failed to do several key things:

I organizationally never prepared myself, my team or the broader program to address any of the cultural intricacies of each university or college.

We needed to roll out this product, quickly. Without clear direction to how people would be impacted on a cultural level.

So instead of designing content empathetically, I simply created teams to push out task-oriented check-lists. I had convinced myself that I had “rolled it out” by clarifying the sections, the timing, and had it all ready to go.

But I never once figured out who was impacted and what to assess. And because it was a such a big project, I skipped over it because I didn’t want to address it. I had exactly eight months to figure out how in the hell I was going to train over 200,000 people with an undefined budget, an extremely short timeline, and an incomplete product.

I know all of us have done this, but I will not lie to you. I was having nightly terror attacks, not panic attacks, but terror attacks.

Because I was going with a classical change management process that wasn’t relevant to the culture of the organization I was attempting to change with enablement.

But my saving grace came from an amazing mentor. She introduced me to modern change management. I was unaware that the processes could be adapted and should be adapted to meet the cultural needs of my audience. It gave me was some frameworks that I didn’t have to recreate.

By the time that I had been blessed with this information from my mentor, I had already wasted 9 months in back and forth and being stonewalled by most of my project partners.

In the end, the culture of the organization was so deeply woven into the day-to-day functions of every university that it overwhelmed me. I couldn’t operate in a centralized locale and had to redistribute the team I had built to each individual university, and ultimately had worked myself out of a job… you don’t need a centralized leader if there is no center, right?

The point is that you don’t have to grind the wheel into the sand. There’s frameworks out there to help you.

And really, the way that I have taken that interpretation of how to structure any enablement project is to put the ‘change’ you are attempting to enable into three major buckets.

an image which says: buckets of change - product, process, people. Below that, an arrow which points left to right, with the text: increasing complexity + time.

Chunking to define how culture changes people

Is it a product change? It could be relatively simple. In many cases, it’s like ‘Uh huh. I show you how to click here. You click there. Yeah, you did it.’

Is it a process change? Okay, this is a little bit more complex. Maybe I need to talk to the managers to get you and the manager to agree.

Then the people. The hearts and minds. And change management will help you immensely there.

But I want to clarify that change, regardless of how it is chunked will always happen to people. That means that you have to frame the impact on people. I believe there are seven questions you should be able to answer to your audience:

  1. Why should I care?
  2. Why do you need me?
  3. Why should I invest my time?
  4. Why should I change my process?
  5. Why can’t I keep doing what I’m doing?
  6. Why is this happening to me?
  7. Why am I making this change?

You have to be able to answer these seven questions. Not only do you need to have the answer, but you need to clearly and consistently document the answer to these questions in your charter for a program or an intervention (a training event.)

If you can’t, maybe sit back and think a little bit harder about how you are going to get the answers for an organizational move.

As an example, let’s say you’re moving upstream. You’re going to start selling to enterprise companies. Can you tell your enterprise reps, your mid-market reps, any of them, answers to this? Can they answer that sufficiently? Not even adequately, just sufficiently.

The reason why I’m using this kind of context, this kind of language, is authenticity.

Most people will react to you, as an enablement professional, by saying they don’t want to or don’t care about the change that is coming.

Thankfully if you are like most enablement professionals, you can counter by clarifying: “Hey I’m not in your upline. Tell me that’s BS. Tell me you don’t care about me.”

Why? Because by labeling and addressing their specific context lends more authenticity to the conversation.

For a tactical sales example, you are probably confronted with ‘we are getting only 60% of our MQLs (marketing qualified leads) to demo. What the heck?! Training will solve this!!’

Hopefully, now that you have my failure to learn from you can now begin the conversation with ‘how is the culture going to react to this a product, process or person change? And then why in the hell should the audience care?’

And once you can answer the 7 cultural questions and have chunked the broader issue into product process or people change, then you can push through whatever it is the audience needs.

Cultural enablement in practice

While I was at Salesforce, I was asked to support the rollout of two brand new product clouds during Dreamforce 2015 and I had three weeks. They asked me to enable about 1000 people, split them up to 500 each into two different product clouds, and prepare them to sell the product convincingly.

Now that I knew that culture eats strategy for breakfast, my first thought was not where to start, but why should they care about doing this?

Well, I had the company perspective… they we’re doing this because they found out through market research that industries-focused salespeople are incredibly successful. In fact, they’re 150 times more successful.

So why should the salespeople change? Well, current practices weren't working. They had simply placed traditional generalist into industry-specific sales calls and asked them to go out into the world with new product clouds.

The motivation for the individual sellers became clearer with more introspection and interviews. Industry trained salespeople were more successful than their generalist peers.

So then why should somebody else invest in making that change? Well, maybe it’s money? Possibly but that wasn’t deep enough. It was also asking them to change their process. So why then changing their process?

Ultimately, what we found out was that this was both a process and a people change. Were people taking the same language? Were they all on the same page when goals had been defined?

After some initial pain, we discovered that that the product marketing group wasn’t even talking to the line management group. They had entirely different understandings of what it meant to go to market and so had differing perspectives on what success would look like at the individual contributor level.

In the end, it was all about getting everybody on the same page. Based on the time spent in understanding cultural definitions we were able to plot a way forward. While the marketing group kept saying “customer”, the superb sellers are like ‘no, if you’re going into healthcare, you don’t call doctors and patients customers.’

This was the biggest lift. Just getting everybody saying the same thing, understanding the same thing, agreeing to the same thing. Whether it’s metrics, definitions, processes. Once we had alignment on definitions, then the next big step is alignment by audience. So who’s doing what, what are they going to be doing and how are they going to do it?

Without going into details, this is where I would suggest that you lean into change management. It’s all there. If you look up change management, do a Google search, you’ll find frameworks for how to do all of this.


I can tell you that you first and second attempts are not gonna work. You gotta give the sales team, the sales leadership, the sales executives the opportunity to muck it all up, because we learn best when we make mistakes.

The other thing is, of course, adoption and acceleration. Crawl, walk, run. Get it out the door, get it at least started, continue to coach, support your leadership team, support them and give them safe places to fall.

Kira's article was first featured on

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