Career Roadmapping: A Systematic Approach to Maximizing Career Potential

Today’s job market feels quite different than it did a decade ago- roles are being automated, remote work presents a new novelty to consider, and major organizational change is not only more common but it happens at a faster pace.?For those reasons employers are going to use every tool at their disposal to encourage or discourage you to change your employment status.?In that vein, recruiters often address superficial needs as a means to generate interest- this is how career misalignment occurs.?

This article is written for folks who are grappling with the idea of initially drawing or recommitting to their “Career Roadmap”.?We’ll talk through the importance of?Identifying Your “Why.”?We’ll jump into a systematic?Search Process?and discuss some criteria you can use for?Decision Making.?We’ll tie up with some tools, hacks, and pitfalls you may encounter after you push off the dock.??

1. ?Identify Your “Why”
2. The Search Process
3. Intentional Decision Making
4. Final Tips to Consider

Step 1: Identify Your "Why"

A year ago a mentor of mine sent me a resume of a young ambitious tech leader that had relocated to Cincinnati- introducing Brian.?Brian’s ‘why’ was simple and straight forward, I’ll paraphrase (Brian was more eloquent than this).?Brian was working for a large CA based Tech firm for several years in San Francisco and had built a great track record of success.?He relocated to Cincinnati with his wife during the pandemic, his wife was a Cincinnati native but he was in a strange & foreign land.?Brian initiated his search for one reason; to be in contention for a promotion at his current employer it would require him to relocate back to a major hub and leave Cincinnati.?Brian experienced what many costal folks before him have- Moving to Ohio from the west coast may be difficult but once you put down roots you fall in love and don’t want to leave.?His goal was to find a management role where he could jump into a leadership track to coach and manage young sales talent.?He felt he had the background that qualified him for the job and the skills to be successful- he stuck to his guns during his search despite the great offers he received to be an individual contributor.?Fortunately for Brian he landed the job he was looking for (fortunately for me it was on my team??).????

?Brian’s case was a simple one, the organization he worked for made an ultimatum to their employees and he responded to it.?Many situations aren’t this simple.?What do you do if you have a 1-2+ year track record for success but haven’t been in consideration for a promotion??What do you do if you’ve been performing but you and your boss just don’t see eye to eye??What if you’re the #1 performer but the next step isn’t appealing to you or you’re ready to step out of line and take a risk, or you want to leave the individual contributor briefcase at home and move into leadership??The stakes in these situations are high.?I’ve seen multiple people fumble and put themselves in jeopardy of losing the equity they’ve worked so hard to build.?Below are some steps to consider when you arrive here:?????

• ?Identify Your Intent & Mission Statement:?In a few sentences identify what are you looking for and why.?Don’t overcomplicate this.?Your mission statement needs to be authentic and simple.?We just promoted a rising star on our team, Colleen.?From when we hired her onto our SMB team several years ago she said she wanted to “move up market, work with larger clients on more strategic deals” and she’s doing that.?She didn’t overthink it and she’s been promoted multiple times in just a few years as she continues her career progression.?Your mission statement should be a few sentences not a thesis.???????
• Talk With Your Mentor Circle:?Now that you can explain what you’re looking for and why, we can get on with it.?Your mentors should be people who have had career success you admire, are familiar with your strengths and weaknesses, and are brave enough to tell you when you’re wrong or unreasonable.?I’d encourage anyone looking for mentors to have mentors both inside and outside your company.?I was lucky enough to have a few mentors in my life that I talked to when it came time for me to make a career change.?Should I be patient or more aggressive??Is there a high demand for my skill set??Should I be more diplomatic??Am I pursuing a career path that will make me happy??These folks will help you with your blind spots, give you ideas you hadn’t thought of, share experiences, or stop you from making major mistakes.?If you don’t have a “Mentor Circle” start building one today.????
• Have the Conversation with your Boss:??This is the stage that people often hit my radar because significant complexity gets introduced as they decide to have these conversations.??If you’ve prepared effectively you should be confident in the conversation that is to come.?You’ve put in the effort and time to establish your intent and mission.?You have leaned on your mentor circle to provide clarity and feedback.?Now it’s time talk this over with your boss.?Sometimes people fear the responses they may get: My boss will put a target on my back, I have told my boss this before and they tell me what I want to hear and then nothing happens, if I meet with another department head about moving out that’s frowned upon.?While every company/manager handles this situation differently one thing is for certain, providing ultimatums or burning bridges never leads to a positive result.?

?***If you are going through this exercise today and are struggling with decisions or how to navigate this please message me on LinkedIn to schedule time for us to put our heads together.?I go through this exercise with folks in all aspects of their career from soon to be college graduates to director level folks on a weekly basis and would love to connect with you to have a similar discussion***

Over a year ago one of my sales leaders had an Account Management position open on his team and we had several internal candidate apply- enter Ryan.?Ryan had a great track record at the company in his past role in marketing.?He was well liked, great in front of clients, always had a positive attitude, and networked well within the organization.?Ryan wanted to take on more challenges at work and luckily had a great boss that encouraged him to do so.?Ryan was linked up with a VP at our company as a mentor who helped him chart out his career roadmap.?His mentor encouraged him to apply knowing his personality and strengths would be a perfect fit for this role and manger to boot.?Ryan interviewed, got the job, and became a top performer quickly.?After a year of success in his new role Ryan interviewed for a promotion but wasn’t selected- however we discovered something more important in his interview.?Ryan spoke passionately about his desire to move into a leadership role in the future.?Because Ryan was willing to have open and honest conversations, he now has his manager and internal mentor in lock step with his career progression.?Identify your Why, talk to your mentors (inside and outside your company), and talk to your boss.

Step 2: The Search Process

Almost a decade ago I was in this exact position- I talked to my boss and let him know the role I was in, the hours, the location, and career progression was not generating the satisfaction I hoped it would have despite being in the role for 2 years.?My mission was to be put into consideration for a promotion and relocate back to Cincinnati.?I was a sales leader with 5 years of experience, 4 promotions, a track record of success, and a mission that I was committed to.?My boss let me know this wasn’t an option. So now what? I talked to my mentor circle at length about my blind spots, about what opportunities were out there, and how they would respond in a similar situation.??

So you’ve examined where your heartburn is coming from and you’ve addressed it head on with a professional touch:??

• Leverage your Mentor Circle- I mentioned mentors earlier but this situation is one of the main reasons you have relationships with mentors.?Good mentors will open up their rolodex to talented mentees.?Their connections will give you the benefit of the doubt, will be more likely to do more intros for you, have the ability to successfully champion your mission in their business, and give you other avenues to consider.?When searching internally your internal mentors will play a critical role in advising you.?Their knowledge, familiarity, and relationships will help open doors that previously seemed closed.?They might have unique insights into future plans and roles that haven’t been fully ironed out.?Lean on them for questions about the past, present, and future state of the business.???
• Network & Search-?Schedule meetings with as many folks as you can because you don’t know where your next connection will come from.?Be prepared to give them your mission statement.?These meetings will come quickly and will likely result in deep conversations or more introductions- both are good; just keep taking the meetings.?Buckle up.?Just like in sales every meeting could be the beginning of a huge deal.?You can’t afford to be anything other than the best version of yourself.???
• Compile Target Lists- Sometimes this process doesn’t go as planned and there aren’t many meetings or they don’t yield a crop.?This could be because you’re still growing your network, you’re new in your career, or because your skills just aren’t marketable the way they are being presented today.?If this is where you land you have two choices: you can sit back and wait for an opportunity to find you or you can proactively search.?Searching for the ideal fit can be a time consuming and intensive process.?If you are committed to being in control of your career and progression, this is the path forward.?The easy motion here is to get onto a job board and begin submitting your resume.?The only time I’d recommend doing this is if you’re looking for an entry-level role and have no real contacts in that specific geography.?A better move is to check your network and LinkedIn to see if there are mutual contacts.?Begin to proactively reach out and meet with these mutual connections.?An individual that we’ve interviewed recently has been working to get into our company and yes, he did apply to the role, but he also looked at our org chart and sent me a message directly that was well thought out.?I took the time to call our recruiter and ensure he was on the books and let her know I’d like to meet with him myself.???????

People who make career altering decisions without leveraging the above steps tend to jump from job to job every few years, their careers tend to plateau, and their long term income potential tends to flatten out.?Whereas individuals that effectively utilize this Career Roadmapping playbook to inform their decisions tend to land somewhere they have the support and ability to excel.?In the next section we’ll discuss decision making criteria you can use to help ensure you make the right decision when the time comes.?????

If I go back to my personal search process 10 years ago.?I networked externally and I met some amazing people who I still talk with today: Jeff Rowe, Fred Wehby, Doug Miller, Val Bogdan-Powers, Janet Jansen, and Greg Wheeler.?After leveraging my mentor circle and networking externally, I probably had somewhere between 8-12 coffee/lunch meetings and dozens of calls with different people.?Fortunately, I didn’t get to the point where I needed to compile target lists.?A few job offers came out of this situation relatively quickly and two rose to the top as the finalists for me to consider.?The next section will discuss that decision making process.??

Step 3: Intentional Decision Making

The time you’re investing into Career Roadmapping potentially has led you to positive conversations with your manager (and maybe with their manager).?Your mentors probably did a few introductions.?Maybe you had a few recruiters make an attempt to generate interest in outside roles.?You might even have a role/promotion at your current employer to consider.?Now is the time to circle back to Career Roadmapping- how do you decide if the opportunity is the right fit??In my last major career search, I listed the below items as my decision making criteria. This helped me to prioritize the right items and not overvalue the wrong ones.?Just like buying a house- if you don’t prioritize the right items you could end up with a house with new bathrooms, a pool but in a bad school district with foundation issues.?Know exactly what you’re looking for before you walk through the first house.??????

Decision Matrix- asses and rate on a scale of 1-5

• Manager/Leadership- To me there aren’t many items more important than this.?A great manager can change your life and career track.?A bad manager (even with the perfect role at the ideal company) can make your day to day brutal and limit your ability to advance.?Get your manager right and a lot of this figures itself out.?When the player and coach relationship aligns properly the sky is the limit.?When you feel immediate trust with that person embrace it.?When the tandem is right it is exponentially greater than the sum of it’s parts.?This cannot be over stressed.??
• Career Path- Is there a path for more??How many people get promoted a year??Am I replacing someone who was fired or was promoted??Is the organization structure very rigid??Are leadership responsibilities fluid??Do new job roles get created often??If a career path isn’t immediately clear, don’t disqualify the role.?Dig deeper into the organization and find answers.?Some companies have high control structures while others tend to get creative with how they build around people.?Some organizations like to pull in free agents while others like the concept of building internally.????
• Role- Obviously the way you spend your time should have a major impact on your decision making.?I have seen a lot of folks in my career pivot off their path to set up their future in two ways major ways.?1.) Taking a temporary step back from a role perspective as a means to get into a good company, leadership group, or industry- these folks often move quickly because they are apt to perform at very high levels, they bring new ideas, can go after low hanging fruit, and cause many heads to turn in a short amount of time so inertia picks up quickly.?2.) Taking on a role they aren’t qualified or prepared for with the confidence they will figure it out.?This is a higher risk option that carries higher stress, probably longer hours as you get acclimated, and may start off a bit more rough.?These jobs become king maker moments if you execute correctly.?Here’s the kicker- if you take a job you’re not ready for you better make sure your leadership team is committed to you, you’re ready to handle the stress, can build credibility with the team you’re supporting, and are willing to commit the time during the first few years.??
• Industry/Product-This was a relevant point for me that I graded companies on because I wanted to work in technology or telecom.?This line exists for two reason- Is this industry growing or shrinking & do I have any passion for this industry.?If you can’t believe in the industry, product, and the impact it can have no matter what role you’re in you’ll have a tough time making a significant impact.????
• Culture- If you can get time with people who would be your peers this will give you a real idea of what’s going on day to day.?Do people have freedom & flexibility or are they doing funnel read outs every day at 8:00 AM??Is the culture to help each other out or to compete with each other? How do departments address conflict??Are people agreeable or aggressive??Are leaders approachable or busy??Some plants grow in the sun and some grow in the shade.?There’s no perfect culture, there are plenty of flavors.?????
• Compensation- Money is important, it pays the bills and provides choices.?I’d encourage anyone to think about compensation as less of a discussion around “how much of my salary can you guarantee me” and?to play the long game on compensation and career trajectory.?That doesn’t mean take a low salary or don't negotiate for more when the time is right.?That does mean ask questions about comp in your next role or about career earnings based on tenure.??Compensation is a lagging indicator of the other items on the Decision Making Criteria list.?If you select the right role, manager, and career path your compensation will grow over time in a steady manner. Where I see issues arise is when people get 5/5 on compensation and they either ignore the other criteria all together.???

Every role will come bearing tradeoffs.?This criteria helped me value the right things, ignore the items that would have a low impact on my happiness, and would impact my ability to thrive.?All of these items are important but some more than others.?The key here is honesty and objectivity.?Whether you’re comparing multiple options or comparing your current role to a new one let this matrix help you ensure you’re finding a better fit and not just taking the first opportunity that hits your plate.?The best decision you can make is to pass on something that isn’t in-line with your career mapping goals even if you are in a search mode.?When you fill the matrix above the results should not surprise you.?The intent isn’t to allow an equation to dictate whether you pursue an offer or not.?The power is in the internal dialogue you go through as you decide exactly what categories are important for you and how you weight them.????

Final Thoughts to Consider:

While everything previously discussed is focused around what you can actually control, the majority of pivotal decisions are outside your control.?Getting a job offer- outside your control, getting a raise- outside your control, being offered a promotion- outside your control.?Career Roadmapping is all about understanding what you can control versus what you can only influence; maintaining a grasp on your “why” and understanding the role that patience and humility can play.?I’ve never been big on placing a high value on fate- I believe in identifying and addressing the controllable factors.?It is not easy to be professionally aggressive in a particular set of circumstances (what you can control) and understanding the key decisions don’t require persistence as much as they do patience and humility.?Patience and humility does not equate to submissiveness and accepting a lower post than you feel you are capable of.?Patience and humility are gracefully accepting the outcome of situations you can influence and allowing yourself to execute on the controllable situation to the best of your ability.

• Consider Recruiters- Key Decisions you make are around your mission, your priorities, and ultimately your future…be cautious when recruiters attempt to adjust these.?Recruiters are a key piece of this situation and the great ones focus their efforts on getting you familiar with key people at their company to see if there is a long term fit.?The people they connect you with should be your primary sources for your decision making criteria.???
• Career Roadmapping vs. Your Day Job-?It’s easy to let Career Roadmapping interfere with your day job, so make sure you’re keeping your feet on the ground during the day.?Never let performance in your current role compromise your future path.?Expect that to make the right decision you should probably be working longer hours or if you’re Career Roadmapping at your current employer you’ve got a mentor that has the ability to influence and advocate for you.?When I talk to the folks I mentor I’ve shared with them their job is twofold- 1.) Perform at a level that you are proud and capable of and 2.) Learn what you’d like to do next.?When we get together we spend an hour talking about different ways to approach their next steps to minimize the time they spend on the roller coaster of emotions career possibilities brings.?Find a balance here.????
• The Role of Honesty and Objectivity?-?As you evaluate options be as objective and honest as possible.?A question I like to ask folks when they come to me at the beginning of their Career Roadmapping exercise is - “How are you contributing to the situation you say you don’t want.”?We all do it in some way, but?being aware of where and how that happens is critical.?Sometimes on paper the role you are designed for doesn’t agree with your ego.?I had a co-worker that went from in individual contributor role into a senior management role. The day to day decisions they were asked to do seemed to frustrate them.?What they were designed and built for was working on more strategic clients, not managing a group of reps.??
• When Considering an External Lateral Move- Job hopping has become much more common.?I see this situation on a regular basis-?A sales rep decides to take a very similar role they are in today with a competitor or in the same industry as their current employer; they stay for 2 years. Fast forward 5-7 years into their future and they have been at 3-5 different companies all within an arms reach of one another.?Folks who don’t deploy the Career Mapping playbook end up flying blind and become significantly more predisposed to do this type of job hopping purgatory.?They overweight the compensation category and underweight other important categories: leadership, culture, a career path, etc.?The equity they worked so hard to build at their first long time company is long gone, they aren’t in contention for promotions because no one knows who they are, or their performance track record simply isn't tenured enough. So what do they do now??Simply put- the difference between taking an intentional lateral step sideways to move forward and job hopping is the way you identify the upside of the manager/leadership, the culture, and the career path.?People who do this right make an informed strategic move while others blindly jump for $5K.????
• The Importance of Diplomacy: Leave emotion at the door at all times during any type of career conversation or negotiation.?These conversations often get heated or cause people to become heightened.?Being professionally honest and direct is different than winning an argument or giving someone a piece of your mind.?The best way to win an argument or get your way is never to have a debate in the first place.?If you are aware you’ll be entering a difficult conversation, writing out a script ahead of time is helpful.?The conversation may not go exactly the way you want but being prepared will help you game plan where you’d like it to end.????

Career Roadmapping is simple...not easy. Please leave some comments below on how this landed on you in your professional situation. Best of luck in pursuing your professional goals!