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.

Kira Greer has a career spanning almost 20 years in sales roles. In that time, she's made some mistakes and shared them with us at the San Francisco SES.

Taking us through the steps she has taken, Kira offered invaluable insights to anyone in a new sales enablement environment.

Here's her story.

"I would love for you to learn how I fucked it up, excuse my language, because I am really good at messing up. But the amazing thing about messing up is that you learn.

You learn amazingly well what not to do the next time.

Ultimately it's picking and choosing battles, and understanding what your game plan is on a grand scale and then figuring out how to get it all to work."

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Enablement is both a catalyst and a capstone

"Why do I say this?

You are thrust into a situation where it's like, we have to enable them. 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.

You want to start with training or you want to start with content, or you want to start with an idea, but ultimately, it's all about starting in one place and figuring out how to navigate to that next one. And what are each of the steps along the way?"

This is one of my more glorious failures

"I had an amazing opportunity to lead the enablement and training for the University of California. That is all 20 universities, laboratories, business schools and law schools. I was tasked with making an ERP transition to PeopleSoft.

All of your California state dollars, if you are a state citizen, a good chunk of it is being spent in just managing HR paperwork.

It was hell, because all 20 universities had their own thing going. And every single University is non hierarchical. There was no structure. The janitor had the exact same amount of say, as the comptroller, or the CFO.

And from an enablement perspective, it was both amazing and positively terrifying."

Where did I start?

"I started with the people.

Because this change was happening to these 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 that, was structured around them.

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 line of understanding about why they should care about these other satellites.

My spectacular failure was this."

Culture eats strategy for breakfast.

"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, which are all about the top down, and I got taken to task.

My initial attempts were complete failures because I failed to do the key things.

I organizationally never prepared myself, my team or the broader program to address any of these things. I was simply an order taker.

We needed to roll out this product. So I rolled it out, figured out the sections, figured out the timing, figured out the entire project. I had it all ready to go.

But I never once figured out who was impacted and what to assess. And it was a big job, so I kind of skipped over it.

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 process that would not apply.

But saving grace, down from the heavens came this amazing mentor. She introduced me to change management. The reason why I want to bring up change management is that the one thing it gave me was some frameworks, consistent frameworks that I didn't have to recreate.

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 it, is I put it into three major buckets."

"Is it a product change? That's really simple in my mind, that'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 ultimately the frameworks are there to help you get everybody.

But it goes from the standard place where most people think of is what's in it for me? I actually would say that this is way too narrow. I believe there's seven questions you should be able to answer to your sales teams.

  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, either in your charter for a program or an intervention.

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.

Let's say you're moving upstream. You're going enterprise. 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.

I'm not in your upline. I'd rather you come to me and tell me to my face. That's BS. You don't care about me. You don't care why this is happening.

Wait a minute, hold on. Let's talk about it. So you say you don't know why it's happening. Let's discuss. And hopefully I'll have the content in place.

For example 'Hey, we are getting only 60% of our MQLs to demo. What the heck, we need training.'

Well, hopefully when you're designing a program you're going with 'Okay, is this a product, process or person? And then why in the hell should the audience care?'

And if you can answer these, you can then successfully make sure in a very short amount of time, you can push through whatever it is the audience needs."


"I was at Salesforce, I was asked to support the rollout of two brand new product clouds during dreamforce and I had three weeks.

They asked me to teach about 1000 people, split them up to 500 each into two different product clouds. We've got to train them.

Okay, first thought, 'where do I start?' Why are we doing this?

Well, we're doing this because we found out through market research that these industries-focused salespeople are incredibly successful. In fact, they're 150 times more successful. Perfect.

So why should the salespeople change? Well, our current practices aren't working if we just simply place them into those new product clouds. Well, duh.

So then why should somebody else invest in making that change? Well, maybe it's money. No. You're asking them to change their process. So why are we changing their process?

Ultimately, what we found out is that the marketing group wasn't even talking to the leadership group. They had entirely different understandings of what it meant to go to market.

It was all about getting everybody on the same page. Based on definitions. 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.'

Duh, was the response. It was one of those simple things that you think everybody's saying the same thing, when in fact, they're not.

This is probably 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.

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?

Lean into change management. It's all there. If you look up change management, do a Google search, you'll find all of this.

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."


"I can tell you without being able to just throw it out there, it's not gonna work. You gotta give the sales team, the sales leadership, the sales executives the opportunity to fuck up, because we learn best when we make mistakes."

This article is adapted from a speech Kira gave at the San Francisco SES, Kira Greer is Head of Sales Readiness and Operations at at Concord