The Wayward Sherpa

Note: I looked up Sherpa, which I always thought was more of a term for the guide/helper one hires to climb mountains, but it appears to be a nomadic race/ethnicity of people. But the word does seem to have strong meaning towards how I am using it. I hope I do not offend anyone.


This is the first in a series of posts I have been wanting to do on the various leadership styles I have encountered during my career.

This is the tale of the “Wayward Sherpa.”

At one company I worked at, we had been through a number of leaders over the years and we to some degree felt rudderless given our latest set of marching orders. Our current leader was still there, but in his defense, his strengths (as I see them) are more for governing and tweaking an existing company, with existing customers, the aspects of building a new business in a new market, I feel he gave it his best shot.

However, in the end, we needed outside assistance. Enter the “Wayward Sherpa”, the hows and the whys of his arrival are neither here nor there, he was going to lead us to the promised land. He was supposed to have a plan ready for us to follow, a map as it were, and contacts that would help our progress in this new an foreign market sector that none-of-use were really that familiar with.

If I can digress a little, the idea that an organization can bring in some kind of “rainmaker” for business is not necessarily a pie-in-the-sky concept, I have seen it where someone with knowledge and contacts in a particular industry have immensely moved forward the endeavors of a company, but generally through partnerships, not sales. I have worked with what feels like half-a-dozen Sales People (sometimes called VP of Business Development), but in the end Sales People all the same, that have the elusive “Rolodex”.

They claim to know fscking everyone, and that knowledge will help us close the deals that we need to really get things going. I am going on fscking record, here and now. It is honestly better to take all your money, fly to Vegas, and choose either Red or Black and bet the farm, than it is to bet on the “Rolodex Play” paying off.

And I make a distinction between the Rolodex and the Rainmaker, because to me the Rainmaker is going to help you forge alliances/partnerships that will lead to deals, while the Rolodex is a sales guy who just fscking finished selling shit to companies that you also want to sell shit to, and if it is in the same vein as what they were just selling, you’re boned until their budgets renew and the contracts expire, eg, you hired them for fscking nothing.

I have more about the Rolodex, but will save that for a post later on.

Point of the digression, is hiring someone with knowledge of the industry you’re going to go after, is a good thing, the sooner you do that the better and I mean more than just someone who happens to have their kid in the same little league as someone in the industry your after (no shit, that is an REAL example, from one of the half-dozen Rolodex plays), they can help guide the company on how to build a product, how to pitch it, how to sell it into that Industry.

But hiring someone with industry knowledge as some sort of last ditch effort, just buy the ticket to Vegas, at least you will get some free drinks, hell might even win enough money to make payroll.

Back to the Sherpa.

So the Sherpa had a plan, it was simple, too simple. Like the kind of comical saying “If it was easy, everyone would be doing it.” Everyone reviewed his plan and we set forth filling in the particulars, e.g. making it more than just the plan from South Park.

As we got a couple of weeks into the Sherpa’s plan. We hit a snag, an EXTREMELY critical part of the plan, the one where we hook up with a particular group/classification of partners that for all intensive purposes the Sherpa swore on a stack of bibles that they existed and were just waiting for a product like ours, that they can make revenue with.

He came out on a call and said “I don’t know if they exist.”

Stop the fscking presses.

Don’t know if they fscking exist. But the plan, the plan that was devised by the Sherpa and agreed to by our board and executive management, the plan that we have been following for weeks, with our burn rate cutting into our dwindling funds (seriously, wish I could have just gone to Vegas), “I don’t know if they exist.”

I am sure I have been called harsher words than “negative” during this era of my career, comically I was dubbed “Ben Crusher of Dreams” by some of my staff and coworker-friends. But yeah, I was never sold on the OVERLY simple plan to begin with, but hey, wasn’t my money and I have a mortgage, so let’s suit up and slay them dragons. (Sorry, I know mixing metaphors.)

As time passed, the Sherpa and I got along less and less. I have to admit, I wasn’t very trusting of him to begin with, as on many levels, I felt the plans presented to me were the strategic equivalent of Snake Oil. But I don’t believe I performed my job any less efficiently or accurately due to my mistrust.

But as the end of the reign of the Wayward Sherpa came to a close. I was presented with a rare opportunity to have one-on-one meetings, fairly regularly with him. And in one instance, it was face-to-face, vs over the phone.

I forget all the specifics, but it went something like this.

Me: So you were hired to lead us to victory.

Sherpa: I don’t see myself as a leader, more of a guide.

Me: Need you to explain that in more detail.

Sherpa: Let’s say there is a mountain over there. 

Me: Ok.

Sherpa: I am here to help the team get up the mountain, I am not here to lead you up the mountain, but to help the team come together and climb that mountain.

Me: Right, but there has to be some known path up the mountain.

Sherpa: Even if I had the answers on how to get to the top of the mountain. I wouldn’t tell you, I am just here to help bring the team together to climb the mountain.

It quite honestly at that point, I stopped believing anything the Wayward Sherpa told me, ever.

Because, as the LEADER (CEO, President, Supreme-Commander of the Allied Forces, etc) it is you job to tell us how to get to the top. And if you happen to be wrong on the way, hopefully it doesn’t cost lives or livelihoods, but you are not being hired to help us up the mountain, you were hired because you have the gumption to LEAD the team up the mountain following your plan, you know the one with the partners that don’t exist, I mean they did, but now they don’t.

Given the mountain analogy he used during that conversation, I coined the name Wayward Sherpa.

So what to take away from this.

If you’re going to be a leader, take ownership of it, don’t just think you’re there to guide a team. You’re there to lead that team, and in some instances that will mean you’re helping department leads/managers vs being in the trenches, but in the end, that plan is yours, good or bad, failure or victory.

Secondly, if you’re working for a Wayward Sherpa, get your resume together. Because, the place you are working, it will limp along until the death rattle and if you have access to petty cash, not telling you to commit a felony, but if you can cover the losses from your own savings account, book a ticket to Vegas, you might save the company.




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