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.




Choose-your-own Career/Adventure

There are no doubt several schools of thoughts around the natural evolution of one’s career in any sort of modern company (namely hi-tech companies).

But the main focus I have is around the idea that the natural evolution of a team member is to become management. The dreaded management, with great responsibility, likely comes more money.

Early on in my career, I was presented with an interesting scenario, that due to my young age, I was told I could not be the manager of the team, and therefore I had to interview a short list of candidates that the VP of Sales had chosen for Director of Sales Engineering.

At the time, I thought I was ready to manage, but I am knowing what I know now, I know that I wasn’t ready. But as I was most knowledgeable in the team (I think there were 4 other sales engineers, but we eventually hired a 5th), so as most knowledgeable, I led training sessions, I coached them through calls with potential customers, basics of doing the job.

At the time I didn’t realize it, but I was basically a team lead, who had the opportunity to hire my own boss. I hired the one that seemed to be the best fit for us in terms of industry background, personality and technical skill. And Larry was good, though when we hired our 5th, I expressed a concern about him and that I didn’t think he was going to be a good fit.

On a small aside, shortly after the 5th was hired, there was a discussion that came up in a team meeting about moving the commission structure to more of a pooled commission system, which I guess on some level, if I hadn’t had some deals closing imminently, I likely would have been in favor of some sort of hybrid where 25% of the commission goes into a pool that the team gets paid out of, as you know in the end, we all help each other. But, as the deals that were about to get paid out, were all mine and had been in the works for a while and with realistically no help from others, I was against it. As was Larry, I remember him telling the 5th not to bring it up again, and in such a way that meant that they had already had a conversation about it and told him that it wasn’t up for a debate.

The 5th later caused more issues and tried to jump departments, by way of a project that had him over at the development office (some 30 minutes away), yet, the project was not making any progress and when Larry would call over there, the 5th was missing. Comparing notes with folks over in the other departments over there, it seemed there was quite a bit of time ‘missing’.

But back to managing vs leading.

I eventually was able to hire/build a team of developers, several iterations of my career later at what I view as almost 5 companies from when I was an unofficial team lead. The company paying me only changed once though, long story for a different post.

I went about reading books and reflecting on what I felt were good bosses during my career thus far. Looking back, Larry was a good manager, and while I didn’t learn anything technical from him, he pointed out areas of professionalism that I could work on and I took them to heart.

I think the two books that had the most impact on my views on hiring/building and managing a team were Managing Humans by Michael Lopp and Smart and Gets Things Done by Joel Spolsky. Those who were close to me at that time might have seem me read and reference other books, but those were either oriented towards marketing or towards general business management, those two books I link in this post are the ones I really feel had a substantial impact.

During that time, I hired nine developer, we didn’t have all nine at once, I think at most we had 4 web devs at one, the general principle was to have one front-end oriented dev and one back-end oriented dev, the two could do parts of one another’s jobs, but to achieve a high-quality piece of digital work, you need specialization.

I also was ‘given’ some staff from other departments, in one instance, this lasted for about two days. And the feedback I got was to the effect of ‘He said you guys were just in Chaos,’ well I guess depending upon what you’re comfort level is for the unknown, yeah we were in Chaos. We were in the middle of building a department and we didn’t know a lot of what we were going to be doing, but to us at that point, it was exciting.

The other, we had him until budget cutbacks came into play, it was against my wishes to have him let go, but it came down from a higher level of management. Aside from being friends with him, I felt the elimination of that position meant that our company/division was going to lose autonomy and on a deeper level, I took it as a sign that we were done, but no one wanted to admit it.

So during this era of my career, I dealt with vacation scheduling, performance reviews, 1-on-1 discussions (fairly weekly), code reviews, write-ups, letting folks go and also firing those that repeatedly failed to comply with company policy.

And out of all of that, I feel that I did lead the team on a technical direction level and I did my best to manage them, but for a time there I did have a development manager, who dealt with the nitty-gritty of the scheduling and making sure tasks were getting completed, because as you grow as a company, those tasks are still all very important, but can bog down the ‘leadership’ of the company, so you hire folks to handle those tasks.

I sort of look at it this way, often Project Management is mistaken for Product Management and a Product Manager is often mistaken for a Project Manager. To which, I personally take offense.

Product Management encompasses the tasks of project management, which means a good Product Manager has to be able to manage a project. But a Project Manager doesn’t generally make any decisions about Product, they are there to ensure the project completes as it was planned.

Leaders can manage, and managers can lead, but realistically you start to reach a level of work and company growth/size that requires specialization, going back to the idea of a front-end and back-end developer working on a web app, it will be higher quality, because while the back-end dev can edit some CSS, it is highly unlikely they will be able to implement a grandiose web design, much like a front-end developer can make the web app talk to the database, but they will likely run into issue trying to design a database and application that can handled significant volume.

With all of that said, what is my point?

I have lead teams (sometimes folks that didn’t report to me or technically even work for my company, eg contractors) and I have managed staff.

I don’t like managing staff. While I was managing staff, I was also trying to do my own job and I was also doubling as systems admin and a level (probably 2nd level, but felt like 1st) tech support for a number of our customers, but was doing that so my developers could continue to develop and I didn’t have budget for staff to do those roles and if I had bogged the developers down, we would have had issues completing our projects on time. So I took it on, removing the obstacles as best I could, per what I learned from Mr. Spolsky.

But given the choice between being a senior level individual contributor and a manager, I feel I would take the senior level individual contributor role, every time. (But given the choice of unemployment and managing staff, oh yeah, I would manage staff, until I could go elsewhere.)

My view on this may eventually change, but it also may not.

I leave you with these words, paraphrased, that were given to me by a VP that I worked with a long-time ago (feels like a lifetime ago), “You have to look out for your career, no one else is going to be looking out for it.”

So pursue what you want to do in life, pursue what you like to do. Every jobs has things that we don’t like to do, but if that is all your job is, things you don’t like to do, seriously look around, you might have to move, but look around.

Some links I found on the concept of Management vs Leadership

Wall Street Journal

Educational Business

Peeler Associates

Leading vs Managing

Chicken and Egg Debate

“Which came first, the chicken or the egg.”

Within any organization, be it a software company, a non-profit animal shelter or a telecommunications service provider, at some point a debate will occur between the various departments that is something to the effect of…

“Without my department’s efforts in getting the money, you would not have a job.”

And the rebuttal is then…

“Without my department, you wouldn’t be able to get the money.”

Within a standard corporation, this debate generally happens between the sales department and the department that is responsible for creating the product.

I actually had the privilege of witnessing a ‘debate’ happen at the very first company I worked for between one of our sales guys and one of the software leads. I believe there was beer involved, I forget, but I do remember it wasn’t a ‘Fsck it I am out of here.” type of debate, but there did seem to be some actual hurt feelings on the part of the sales guys.

I have by proxy witnessed the debate happen at other organizations. I mean it is inevitable, the debate will happen, as folks want to feel that their work is important and special. But the issue is, all the departments are important, so they are all necessary parts of the picture to make money, regardless of profit or non-profit.

I generally feel that the best way to end the debate is for someone to point this out to the parties involved and to try and congeal the departments at a unified team, but to accomplish that, you need a true leader. And to be quite honest, true leaders within the business world are few and far between. There are those with the title that can rule through fear (eg, do what I say or I will fire you), but for those that can inspire others to go above and beyond because they just feel compelled to do so, that is true leadership.

I’ll write more on leadership later, but for now, the debate happens, how it ends is more important.