How Douglas Cole Sells: Strive to Be Objective, Not Likable

Douglas Cole was a consultant, an MBA graduate, and an entrepreneur. But, as he reflected on his career trajectory, there was one area in business he hadn’t directly tackled yet – sales.

“I wanted to see what growth looked like on the front lines,” Doug said.

So, in January of 2017, he jumped into enterprise selling at LinkedIn. He hasn’t looked back since.

“I found it unexpectedly exciting,” Doug said. “In short order I learned that sales is this interesting combination of psychology, strategy, and systems. Those are all things I like a lot, and that’s why I’m still having fun.”

He also succeeded at it. After surpassing quota multiple quarters and making President's Club, he was promoted in October of 2021 and now leads a team of LinkedIn enterprise relationship managers.

On the side, he teaches courses on consulting and sales at the University of Toronto and at Schulich ExecEd. And he just recently published the book The Sales MBA , which focuses on how to influence corporate buyers.

So, how does Douglas influence corporate buyers? What drives him daily? What was his biggest failure in sales, and how did that transform him?

We asked him all of that and more in our latest edition of How I Sell :

1.?What motivates you to come to work, even on the days you'd rather not?

I like to arrange my life so that I'm not relying on my motivations day-by-day. Instead, I like to set myself up so that I'm falling back on recurring processes and systems.

All these systems – from my workout routine to my morning routine to my quarterly fasting routine – are designed to reinforce a sense that I'm in a constant state of becoming. This protects me from the risk of not feeling motivated in a given moment.

2. What's your sales philosophy, in 3 sentences or less?

I would say the best sellers are strategists, change agents, and decision architects, and that their revenue achievements are simply the natural consequence of living out this elevated view of themselves and their craft.

3.?Is there a common mistake you see sellers making? How do you suggest they adjust?

One of the more common mistakes I see – especially for people who are relatively new to sales – is a tendency to want to be likable rather than objective.

I was just listening to a Gong call the other day, and the seller was working with a new client. The seller was clearly trying to build credibility with that client, saying, “Look, I could ask you to buy these additional records, but I'm not going to do that. In fact, I don't think you should buy them. I don't think it's in your interest to do so.”

This seller was banking on the belief that by advising against a sale, he was proving he had the best interests of the client in mind. It was a calculated way to demonstrate he was a likable and trustworthy person.

That was a relatively innocuous example of this tendency. Sometimes it can be a lot more over the top. But I think, generally, it's better to be objective.

So, in that particular instance, instead of saying to the client, “Look, I don't think you should buy more of X,” he could have said, “What needs to be true for you to know that additional records would make sense? I want us to get the best answer for you and your business.”

I think building towards a common understanding of what is objectively important to the?person and the company is a better approach than just trying to be the likable guy or gal.

4. What excites you most about the future of sales?

I'm excited that the sales industry is finally getting the credit it deserves. Up until now,?sales has generally been disparaged and ignored.

In terms of being disparaged, I remember reading a Harvard Business Review classic called Marketing Myopia by Theodore Levitt, which came out in 1960, I think. It’s an iconic, influential book in which the author makes the case that marketing is when you put the buyer's interest first and selling is when you put the seller’s interest first. He claims that selling is basically just a bunch of tricks to get to a transaction.

That was the consensus wisdom at the time. And even though it was written in the 1960s, you can see that the perspective still lingers. There's still a reputational problem that afflicts the sales industry.

The other point is that sales has been ignored. For example, I did an MBA, and sales never came up as a topic. If you look at the roughly 4,000 colleges and universities in the US, fewer than 10% of them have sales programs.

So, again, historically speaking sales hasn’t been given much formal attention academically, and it's a profession that has been casually disparaged.

I think that's finally changing. I think sales is finally getting to a point where people recognize it’s a craft. Increasingly, and I would say appropriately, it’s seen as a legitimate and honorable profession.

People who are good at sales are able to see things from the customer’s perspective, and on multiple levels. They're able to understand the external environment, and they can talk and act like a strategist. They're able to understand the organizational environment, and they can talk and act like a change agent. They're able to understand the interpersonal dynamics, and they can talk and act like a decision architect in the way they frame their information with clients.

So, I think sales is not only a legitimate field, but also quite a sophisticated field. And I think that's finally being recognized. I'm excited about this shift in the consensus.

5. What’s a piece of sales advice you've never forgotten?

I once had a manager who boiled it down to this simple question: “What else?”

I think that is such a powerful pair of words because sales is fundamentally a game of probability.

You're constantly making bets on the future. You choose which accounts you're going to focus on. You forecast your results. You have to constantly update the forecast, and there's this unrelenting focus on the future, which means?you're always, always exposed to risk. You can never be 100% certain that something you expect to happen or want to happen is actually going to happen.

That means you have to be always de-risking the future. And this is why those two words are the most powerful coaching words in sales. De-risking the future is a never-ending responsibility. It’s a Sisyphean task.

Who else can I talk to? What action can I take today? Even when it's at the point where I've prepared the ROI analysis, made the final pitch, and the proposal is sitting with the buying committee as we speak; even though all that may be true, there's probably still something else I can do in to keep the attention on this proposal and keep the energy alive.

That piece of advice has always stuck with me.

6. What Sales Navigator feature do you find the most useful? Why?

I think alumni connections.

By alumni connections, I mean alumni understood in various ways. Not just who graduated from your college, but people who previously worked at the same company you did, your previous colleagues, or past customers who have moved into new companies.

When you look at all the different kinds of relationship intelligence at your fingertips in Sales Navigator, I find alumni paths are most reliable in getting people to respond to you and help with your sales process.

For example, someone on my team was recently stuck on an account, not really sure what to do next. The account had fully churned and we had lost a lot of revenue.

I went through Sales Navigator and found someone who used to work for the client but was now at LinkedIn. He got me in touch with someone else, and that person gave me a very detailed overview of the entire buying committee.

That allowed us to get back in and re-sell the program.

So, for me, the alumni angle has always been the most actionable and direct path.

7. Is there any habit you have outside of work that you believe helps you perform better?

I think the keystone habit is managing energy. That’s the lead domino for performance and fulfillment .

The most important change I made in my life about six years ago was standardizing a 5 a.m. wake-up time.

Seven days a week, 365 days a year, I now always wake up at 5. And it has made a huge difference.

I could feel the impact pretty much immediately.

Before the change, my wake-up time was negotiable. On the weekend, I'd wake up later than during the week because I wanted to catch up on sleep. But every Monday I would shock my system with an early wake-up call, starting the week with a sleep deficit that would continue to accumulate until the following weekend. And then the cycle would repeat.

Now the wake-up time is non-negotiable. It doesn't matter what happened the night before. By forcing myself to deal with consequences, I make better sleep decisions overall. And when I falter, I either take a?power nap during the day or work to get back on schedule very quickly.?

That simple habit shift has had a huge impact on my energy level.

8. What has been your biggest failure in sales and how did that experience transform you?

I think my biggest failure was not beginning with the end in mind.

I can tell you a story about this.

One Friday, at the end of the quarter, all of my colleagues were at the bar celebrating. I was the only one still at the office waiting for an order to come through.

I sat there biting my nails, hoping to hear from the Head of Procurement

Finally, I couldn’t take it any more. I had to call him directly. I went through a bunch of emails until I found his cell phone number, then I took a deep breath and dialed. I was relieved when he picked up the phone, but I could easily visualize his expression and demeanor on the other end of the line.

It was Friday afternoon, he obviously hadn’t recognized the number, and he probably thought it was a personal call since we were so close to the weekend. I told him who was calling. There was a long pause, and I could hear him say “Oh God,” venting his pain at the sound of my voice.

I remember thinking, “I'm never going to let this happen again. I'm never going to let my lack of operational discipline get to the point where I’m forced to put myself in this humiliating position. From now on I'm going to play from ahead so I can go to the bar on a Friday with everyone else.”

So, I think it all comes down to starting with the end in mind and working backwards from where you need to be by a certain date. And then ensuring you deliver.

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