Question: How Do You Move Up The Ladder?

My Twitter friend from the UK, @itsamatar, asked me this:

I’m inspired by your journey from intern to VP to MG and wanted to get your advice on how to move up the ladder from your experience. I’ve been stuck in Infrastructure and Technical roles for nearly a decade and want to know if you have 5-6 tips I should implement that would increase my chances. Thank you 🙂

That’s a good question and it probably has a million answers. My journey, which drives my answer, will undoubtedly be different than your journey.

Walking down memory lane, I remember well my interview to become a web dev intern. I was working at a comfortable job that maybe could have been a career, although it was not anything I would have enjoyed for a long time. It was the typical massive organization where you kind of wait for people to get promoted, retire, or die in order for positions to open up.

I found out about the internship position because I asked my professor, on a Saturday morning as we were both walking away from the school, what I could do to enhance my career. I have no idea why I hadn’t heard about this internship before… probably because the computer professors only told the top students to apply. Apparently I wasn’t on anyone top list of anything. Alas, I found out and was in an interview on the following Monday.

I remember getting out of my junker car in a horrible suit and just laughing… why in the world was I interviewing? I already had a job… But I went in, did the interview, even had one memorable and horrible answer, and long story short got the internship.

My boss was straight from heaven. She treated me as if I were a full-time employee, not a college intern. She gave me real projects and put me in situations where I could really understand web dev. Even though I lost all of my benefits, and made less per hour, than in my big-0rganization job, this was an amazing opportunity.

My next job came because my cubicle-mate got a call from someone who wanted him to do some freelance web work. My buddy had zero interest in doing anything like that but I was hungry for it. That turned into my next real job… the first IT Manager of what would become a $300M organization. First, I went in as a contract developer, but it was clear I became their trusted IT voice, and was brought into a lot of cool opportunities. When my contract opportunity was over, I think maybe 6 months later, I was getting ready to graduate and move to Texas (my dream was to work with Dell Computers in Austin). I sat down with my boss and said, “You guys HAVE TO hire someone to replace me, and be an IT Manager. You can’t go back to having five IT vendors who just blame each other for any computer issues.” He totally agreed. He asked me to write a job description, which I did. Then he asked me to put a salary on it, which I did. And then he asked me to stay… please don’t move to Texas, stay here in freezing Idaho.

And so I stayed. I got the job I created at the salary I made up. And it was a fantastic run.

Our vendor approached me and floated the idea of our company acquiring his tiny little IT shop. That is its own story that should be in a book… long story short, it was a mess. But I was in MBA mode, and very interested in owning our mission-critical software to have more security (“What if he got hit by a bus? It all depended on him.”) and more control over the roadmap to meet our growing needs. Lots of drama during this process and my job was in question. Long story short, I stayed around and chose to work in the newly formed subsidiary (as opposed to staying in the big company and being the main contact for the subsidiary… a role I figured would be a rubber stamper with no executive involvement).

At the new company they asked what role I wanted… having read CIO, the magazine, for a few years, I said “why not CIO?” And so, like that, I became CIO of an organization that had all of 17 employees. I really was young and had horrible mentoring at the time. While I think I did a fine job, it wasn’t like I was CIO of an successful, big organization. Later, I can’t remember why, VP was added or amended to my title. Nothing else had changed.

After about 18 long months the CEO left the organization and I was offered his role. I asked to be CEO or president but the big organization CEO pointed to his hair and said “you don’t have enough of this.” Gray hair. I wasn’t old enough to have that title. Plus, he said, his other execs of the big company would be jealous/mad that I had a president title.

So I was “general manager.” No pay increase because the company was a mess.

That is how I got my titles. I kind of cared about the titles, but as far as the work went it was just work. No matter my title I loved doing strategy, vision, running operations. I had an amazing team of developers and we had a lot of fun, and a lot of hope for the future.

But, as they say, “nothing gold can stay.” My old boss, who was also an owner, came back and politicked for his job back. Ruthlessly. I was busy trying to right the ship and he was busy trying to get his paycheck back. The big guy decided this old boss should have his old role back because, well, I wasn’t an owner, and so how could I possibly be as passionate about the company success as that old guy.

The drama, seriously.

And thus ended my executive career in Corporate America.   Easy come, easy go. I think they gave me the old beat up laptop I had been using and maybe one or two paychecks as severance. And a swift “don’t let the door hit you…” on the way out.

My next phase of titles was owner, founder, president or CEO… of just me. I started JibberJobber a few months after having been laid off. I had one developer and one QA person, and then me and my phone. I was on a call with a friend/recruiter a few years later and said “what kind of job could I even get??” and he said “dude, you are a product manager! Look what you’ve done with JibberJobber!” I loved the idea of product manager… you get a bit of ownership, and a lot of varied duties… and you get to create stuff.

In 2018 I was offered a role to build something but I wasn’t on the PM team, which was very different, so my title was “program manager.” Not super common, but whatever. I didn’t care what my title was, I just wanted to create one of the most amazing, industry altering things that we could have created. But, a few months after I started my boss announced his departure, said he had hired me to replace him, and good luck. The execs decided to kill the entire program and my team was booted.

I was not a program manager anymore.

My titles have been cool, and impressive. But back in 2006 when was looking for a new job my last title was “general manager.” I remember sitting in a job club next to a guy 20 years older than me, and his resume looked the same, except he was a real general manager with 20 years more experience.

I realized my titles at tiny companies in small towns for just a few years wouldn’t even compare to his experience.

Having said all of that, let me address your question. I’ve seen this play out in the careers of others… here are the five or six things you can do right now:

Declare your intentions

Make your path public. Let others know that you want to move up and out. This could backfire if you work with idiots, but generally if management knows you want to move up, they might decide to invest in you and your future. They also might worry that if they don’t have a place for you that you’ll be a flight risk, but that’s less of an issue now than it was 20 years ago (because everyone is a flight risk now).

Be strategic about who, how, and when you declare your intentions. Maybe you do this with your immediate boss, in a one-on-one. Maybe you talk to other executives. Maybe you DON’T tell certain people who might sabotage your intentions. Definitely tell YOURSELF, and believe in yourself

Find Mentors

Not just one mentor, multiple mentors. Some might be in your company, some might be in the roles you want, others might be in other industries (or even at competitor orgs). This isn’t formal coaching… this is mentoring. You have a lot of heavy lifting to do, and you’ll get value as you put in the work. Be smart and strategic about what you can get from (and give to) your mentors. Be respectful of their time. And be appreciative of the wisdom they’ll share with you.

It will be your job to determine whether their advice or ideas will work for you. Be open and humble, and willing to try, but also learn and know for yourself. The outcome of what you choose to do will have a huge impact on you, but not necessarily on them. It is your responsibility to do the work, and think critically about your next steps, not theirs.

In my mentoring courses on Pluralsight I talk about how mentors come and go. You might find a mentor for speaking, a different mentor for strategic thinking, a different one for negotiating, etc. Some might be good for one meeting, others for years. Be flexible how you approach this, and learn as much as you can.

Take classes

If you want to go into management you might get value out of taking some finance classes. This is probably the topic I see most executives struggle with, but the ones who understand finances have a lot of influence. I don’t know your strengths or weaknesses, but whatever your weaknesses are that would impact your ability to move up the ladder, see what classes you can take to fix that. You might find college classes (which might carry more weight with some execs), Pluralsight courses, etc.

Leaders are readers, they say. You need to learn, the rest of your life. I’m guessing you are excellent in your hard skills… list what soft skills you need to go deep on and get serious about those.

Volunteer strategically

I’m not talking about volunteering by serving food to homeless people… although that’s great, too. I’m talking about going to the org that helps homeless people and volunteering in an executive, board, or leadership role. Volunteering might give you opportunities to lead and direct at a level you won’t get at work… yet. You can learn, try, grow, etc. in your volunteer role.

You also prove you really want those roles and responsibilities. And, mega bonus: you might meet people who will have an influence in your next leadership role. The people who tend to have those volunteer positions are people who have leadership influence in their organizations.

A word of warning… you’ll probably be known as “the tech guy” and asked to do all things tech for the organization. Be very careful to not get pigeon-holed in that role. Make it clear that you are there for a leadership role, not a behind-the-scenes network role.

Speak and teach

Speaking and teaching involve a lot of soft skills you should develop as a leader. I strongly suggest you join a local Toastmasters chapter and actively participate. Be uncomfortable, stretch yourself, and be a better communicator. If you are great now, go for excellent. Every leadership role you would have will be enhanced by your ability to speak in small or large groups, and the confidence in communication you get from that training.

Teaching will help you refine how you communicate to individuals. One of your (our) problems is that, as a technical expert, people expect you to talk in ones and zeros, and have a hard time talking normal with humans. This is a stereotype you can break by learning better communication. More than once people have asked me, after I spoke on stage, if I really had been a developer. They were shocked that a developer could have communicated on stage like I had. Bad branding precedes us.

One final thought

I’ve talked to plenty of people who wanted to go from technical to management, and then hated it. If you hate it, that’s okay. Just go back. When I went from technical to management, there was no backward path. I was out of tech too long and, while I was okay to manage technicians, my technical days were over.

I hope this helps, and I hope you get the rich results you are hoping for! This is your career, your path. You get to write your future.

Good luck!