Thinking of a career shift? Here’s how to increase your odds of success…

Every so often people ask me for career guidance. I guess I’ve done pretty well charting my own career path, so far at least, and folks want to know the ins and outs.

Well, here’s a shortish post that captures how I usually answer the question.

The Power of the Adjacent Possible

Usually I start off by talking about the ‘adjacent possible’ – all those roles that are close enough that they’re within reach based on responsibilities, transferable skills, exposure to different parts of a business, etc.

How do you navigate the adjacent possible? Lacking some long-term dream, my suggestion is to base it upon an understanding of what you like and don’t like.

Also, don’t typecast yourself…that kind’ve thinking leads to nowhere.

Understand the Timeline

I usually remind people that they’re generally near the the beginning of their careers, so they should think more about how many more years of work are ahead, rather than thinking about what’s been invested so far.

At this point, I usually remind people that they’re generally near the the beginning of their careers, so they should think more about how many more years of work are ahead, rather than thinking about what’s been invested so far. Many people are of the mindset that, “I just went to school for seven years, and I’ve worked for a few years already…gah, I’m 30! It’s too late to change now!”, rather than, “Well, I likely have 25-35 working years in front of me, so it makes sense to explore what will really make me happy, even if it takes a few years to increase my qualifications.”

I saw an article years ago in which the author recommended that people actually physically draw out their timeline: from birth, to the present, to the expected future. Doing so is a visual reminder for many that they’re still pretty early on in their career.

Chase the Right Thing

Also, provided it’s possible (and I know that situations vary), I encourage people to pursue happiness/enjoyment/contentment rather than money. Can you pay your bills and set a little aside for the future? Well, what if you change your lifestyle a bit? It’s good to keep in mind what’s really important – that new car, or being happy for the huge chunk of your waking life you’ll spend working?

Outside Forces

Of course, making a shift won’t be easy, because unless you’re going the entrepreneurial route it isn’t up to you alone; that is, other people are going to play a significant role in your fate.

Of course, making a shift won’t be easy, because unless you’re going the entrepreneurial route it isn’t up to you alone; that is, other people are going to play a significant role in your fate.

Thinking off the top of my head, there are at least three things that probably have to be in place for someone to significantly change their role:

1. A hiring manager who’s willing to look at transferable/applicable skills, ahead of academic qualifications and professional titles. This one probably comes down to personal characteristic more than any other factor – some people see it, some don’t. Keep in mind that it’s hard for a hiring manager to ‘sell’ internally a hire who doesn’t have the ‘requisite’ qualifications…which brings me to #2.
2. A personal advocate. It could be the hiring manager, or someone else within the organization…but someone’s gotta vouch that the manager or company should take what will be perceived by others as a risk.
3. Persistence, because it’s not always gonna work out. That’s life…so maybe you get nine “no” responses before a “yes”…but really, who cares how many times you hear “no”? You only need one “yes”, and from that point on you’ve got the professional title/experience that everyone’s looking for when they go through candidates.

Aggression and Realism

Don’t get down on yourself, but don’t get unrealistically optimistic, either.

I also reiterate that folks need a combination of being aggressive/optimistic about their transferable skills and a realistic assessment of those skills. Don’t get down on yourself, but don’t get unrealistically optimistic, either. And if you find some gaps that are preventing your career evolution, look for ways to fill those gaps: volunteer experience, continuing education, starting a side-hustle, etc.

When one hiring manager challenged me to defend a résumé point about my time management skills, I explained that on top of being a full-time student in a very demanding program I also had a part-time job at an arena that regularly took 20-25 hours a week. Very few people in my program had outside commitments of that magnitude. That answer helped me make the jump from software engineering to project management.

Later in my career, I knew people would be concerned that I didn’t have professional experience as a people manager; I made sure folks knew that I’d built and led a very successful local soccer club made up of multiple teams and dozens of players. I’ve said it elsewhere, and only partially jokingly, but if someone can handle the egos of a bunch of competitive and recreational former playground legends, then they can handle people in a professional environment.

Think Lateral

It’s worth pointing out that part of being realistic is thinking laterally, rather than upwards. You’re much less likely to be able to jump from being an individual contributor in role A to a manager in role B – that’s just too much risk for the hiring manager and organization. You might even need to step down a rung, but I’d suggest doing so only after a conversation that opportunities will open up once you’ve proven your capability.

Stay in the Same Company, or Move?

Either or, really. It seems reasonable to think that you’re going to have more success making a lateral move internally, where your reputation is known, but sometimes internal ‘dynamics’ get in the way.

For instance, I’ve seen on a few instances cases in which people want to move internally, but then they get stymied because they’re seen as being just too valuable in their current role. Of course, what happens is that instead of moving internally and staying with the company, they just jump ship and the company loses a great employee. Not smart!

The Reality

It’s tough, and I know that.

A friend of mine was trying to make a shift from one marketing role to another, and he had a really tough time getting people to consider him seriously. Everyone who met with him came away impressed, and figured he could do the job very capably, but the hiring managers were uneasy hiring someone who hadn’t done that exact job before – despite ample transferable skills, quite a bit of informal experience in the role, and a very well-developed understanding of the role itself.

Hiring managers are, by and large, tremendously risk averse

Hiring managers are, by and large, tremendously risk averse; they don’t want to have to fire someone later or look bad for bringing onboard someone who doesn’t work out, so they play it safe…that’s why so many of them screw up their hires. Rather than taking a small risk on someone with an enormous ceiling, they hire someone who’s done that job before, even if they’re kind’ve a dud. Then they get what they hired: predictable mediocrity.

Even with strong internal advocates, it took many months for my friend to get hired into his desired role. The company’s hesitation very nearly cost them an amazing employee who’s going to blow them away.

So persistence pays.

And to any hiring managers out there, use your brains: you know what characteristics and skills are needed to do the job, and it usually doesn’t come down to academic degrees or exact former job titles. Keep an open mind when going through applications (and I recommend you go through them yourself, rather than having HR pre-screen) and you might find the next star.

And to any hiring managers out there, keep an open mind when going through applications and you might find the next star.

About Lee Brooks

Lee Brooks is the founder of Cromulent Marketing, a boutique marketing agency specializing in crafting messaging, creating content, and managing public relations for B2B technology companies.