When the work doesn't mean something to you

At the end of my first year as a Strategic Account Director at LivePerson, my manager and I sat down to dinner at Eataly in Chicago's River North neighborhood after an important meeting with United Airlines.

He said, "Brandon, you probably don't even recognize it, but the accounts that you really care about, you are a different seller in front of them. And you're visibly flat in front of the ones you don’t."

I was working on winning new business with two airlines at the same time.

Delta was my number one target obsession when I joined the company. I flew them all the time, loved the brand, and got creative, building all kinds of interesting assets for them.

Just a few months after I started conversations with Delta, United came in through an RFP. I hadn’t been nurturing them at all. They were on my list, yes, but we only started engaging because one of their VPs had used LivePerson in a prior role.

My manager attended both sets of meetings, so he could see how much I wanted Delta. He also saw that I didn't really want to do business with United because I loved Delta so much.

We won Delta that same December.

His feedback stung, but it was absolutely correct. It got me thinking. I had a list of 50 accounts across multiple industries, and I couldn't service all of them.

Until then, I had picked where to spend my time for business reasons only.

Over the holidays, I did something different. I started thinking more like a designer, using systems. I wrote down five criteria that mattered to me—some personal, some business.

Every account got one point for each criterion it met. The ones that scored five became my Diamond accounts, and that told me where to put my time, energy, and attention.

I felt energized going into that next year, and it became my first million-dollar earning year. When things got hard, and I knew I'd be traveling for these accounts, I kept going. I've found that when you layer in the personal reasons you're in there doing the “dirty work,” that's what keeps you going.

I also started to show up better for United after that tough conversation with my manager. Although I was blinded by my obsession with Delta, I did start to care about the airline industry, and I was determined to deliver the highest standards possible for United. I won United one year after that dinner, and I thoroughly enjoyed working with their team.

I told that story on a coaching call this week. A seller I coach walked me through his calendar. He color-codes every block, and the green ones—his revenue-generating activities (RGAs)—made up only a small part of the week. When I asked how he decides which accounts get his time, he said he ranks them by “how likely they are to spend money.”

That's how most experienced enterprise sellers do it, and it's a decent start. But the biggest switch I ever turned on was adding personal motivation.

So I gave him the same exercise I went through, and an order to work in. Human first. Professional second. AI third.

This client told me his energy has been low this year.

He's an experienced enterprise seller with a strong record. His market is tight, and his customers are cutting budgets. Most of next year's number has to come from a handful of accounts he was handed recently. The executives that matter don't even know him yet.

In the account he likes most, his company has a good relationship with one technical team in Security. That team runs the product, but they don't own the business problem it solves, and they won't sign off on a bigger deal. The people who will are elsewhere in the company, and those doors aren’t open yet.

He has to reach them without going around the team that trusts him.

He isn't short on tools. He uses AI every day, and his meeting notes go straight into it. But using another tool won't put more green RGAs on his calendar. Adding more is not the answer. Getting clear on “less, but better” will.

He's low on energy, and he's sitting on a pile of stuff (meeting notes, financial reports, his company's material) with no clear way to turn it into one artifact an executive would act on.

We didn't start with the account. We started with his calendar and designed what elite looks like from there.

Before any strategy, the undistracted work that matters needs a specific block.

I asked him when he does his best work and gets into a flow state. For him, that’s typically mornings, from 9 to 11 am. So that's the block to utilize. Tuesday, Wednesday, and Thursday: 90 minutes of deep work on one account in that window.

The ritual before each block is simple:

The timer matters. My client and I have ADHD, and hearing it start is what tells the brain it's time to work. Starting is a (worthwhile) “tax” you must pay. The payoff is the flow state on the other side, where the work is actually fun, and it rewards the hard work it takes to keep going when it’s easier to skip out.

Professional athletes train this way. Showing up for a training session is often harder than the game itself. We're business athletes. We have to show up for ours too.

Next question. What goes in the block?

He pointed out, fairly, that he doesn't have 50 accounts to choose from. He has a handful. The Diamond Hunter exercise still helps. With a more focused list that incorporates personal criteria, he brings in more “life force” into his sales approach.

This was borrowed from the Japanese concept of Ikigai, and it’s often overlooked. Without this life force driving you and helping you to understand why the work matters, it’s a fast road to burnout.

In my experience, it’s also when most sellers pack it in, think they need to find another role at another company where the grass is greener, and the cycle repeats. And before they know it, they’re 55, feeling stuck, and still leasing their life to others.

Being a Purposeful Performer is how you break that lease and eventually move from earner to owner. It all starts in the small quiet moments nobody sees.

Now for the work itself.

When I was at LivePerson, several Amazonians came over, and we adopted their writing culture. That meant six-page memos, which are really hard to write. Everyone reads them in silence at the start of the meeting. No slides.

They brought one more thing, and I stole it for sales. It's called the PR/FAQ. Before an Amazon product team builds a new product, they write a one-page press release dated for the launch day. Then they write the answers to questions customers will ask, and the hard ones their own leaders will ask.

Here's a sample of how I adapted it for sales.

Write the press release your customer would put out one year after they go live with you. The headline says what they did. The subheading says how you did it together. It needs a quote from one of their executives, so find what that executive has already said publicly and build from it. Keep it to one page. Say as much as you can in as few words as possible.

For a new account with no engagement, the goal is to get it to 60% ready on purpose. The other 40% is the invitation to go do your job. Who do I need to contact? How do I start the conversation? How do I fill in the numbers?

→ The Simple Strategic Selling System may help.

Once you've built trust, you bring it to your Mobilizer, the champion of all champions inside the account, and they help you fill in the blanks. Now you're building it together.

For this seller, the page does two more things.

A great PR/FAQ takes time. People who did this inside Amazon will tell you the best ones took months of drafts. That's the point. Even if nobody ever saw the page, writing it would make you much better inside that account.

Do this work yourself before you hand any of it to AI. Paying that “tax” makes you think and speak more clearly. Then, when you bring in AI, you stand out from the slop everyone else is publishing.

Human first is what my manager pointed to that night over dinner in Chicago. You start with what fills your batteries and what drains them, before any tool gets involved.

Professional second means you get rewarded for paying the hard "tax" of doing the thinking and the creating yourself, even if the first few iterations are messy and ugly.

AI third means you then bring in AI to polish, research, train, and develop. Then you repeat the loop until you have an elite-level artifact that helps you to stand out.

That order is what the next learning path, Human First AI Fluency, is built on. Every lesson has to pass one test: Does it make you more valuable, or less? More to come soon…

Stay human, friends.