I may be one of the few career advisors who regularly encourage job seekers to break the rules.
Not because I don’t understand the rules.
I understand them well enough to know that often rules and conventional wisdom need to be questioned.
I’ve watched too many talented people follow perfectly acceptable job-search advice and end up competing with hundreds of other people doing exactly the same thing. I believe and always tell people to stand out, to own their narrative, and to use all of the tools possible; and this makes me an exception in a world where most career advisors routinely hand their clients instructions for fitting in.
There is something wrong with that.
So, I ask my clients different questions. What if you don’t apply the way everyone else applies? What if you contacted the employer before there was a job posting? What if you stopped trying to make your résumé look like every other résumé? What if you approached the interview as a conversation rather than an audition?
What if the thing you’ve been taught to hide is actually part of what makes you valuable?
Often they look at me as though I’ve suggested something slightly crazy.
Maybe I have.
But here’s what I’ve learned: you can’t ask someone to take an unconventional path without first giving them a reason to trust you.
That’s where the title of this piece comes from.
We move at the speed of trust.
Through experience and training, my approach often lets me see an opportunity before they can. I can see a different route before they are ready to leave the familiar one. I can see possibilities that their previous experiences have taught them not to see.
But none of that matters if I try to drag them there. My job isn’t to convince them that I’m right.
My job is to build enough trust that they’re willing to discover whether I’m right with me.
I’m not asking them to trust me as an authority. I’m asking them to trust a process of exploration.
Building this trust doesn’t make people move faster. It makes movement possible.
Sometimes it will help them to move faster; sometimes they’ll take three steps forward and two backward. Sometimes, and hopefully, they’ll challenge my ideas. Sometimes they’ll ignore it completely.
Sometimes, weeks later, they’ll come back and say: “I tried what we talked about.”
This is the breakthrough, not because my advice was proven correct, but because they trusted themselves enough to try something different.
I think the key is building the relationship between advisor and job seeker, discovering the courage to challenge conventional wisdom, and seeing what happens when we stop treating people as people who need to be fixed and start treating them as people capable of discovering their own way forward. It takes a while to get here.
I find people don’t necessarily resist advice that is unconventional because they don’t want help. Sometimes they resist because accepting my advice requires them to trust me, trust my process, and ultimately trust themselves.
PART I — THE QUESTION
Why don’t more people use cover letters? This is an example of an assumption that most job seekers rarely question. The reason I hear most often is that many employers do not ask for them. They do not see the need because it isn’t a requirement, so they assume that it is okay not to include one, despite the evidence that using a cover letter specifically to tie their skills to what the employer is looking for would seem to be a good idea.
Recently, I had a job seeker brag to me that they had sent out 80 resumes in one week. He had expected praise and was surprised when I asked how many resumes were accompanied by cover letters. His answer was none – because none of the employers asked for one.
It often takes me weeks to convince people to use this basic tool; such is the power of conventional thinking. I explained it several times, and they still aren’t doing it. I have often asked myself and them: Why won’t they listen?
I used to get frustrated before I realized I needed to ask a different question: “What if the question isn’t why they won’t listen? What if the question is what haven’t I earned yet?”
That is the doorway into trust.
PART II — RESISTANCE ISN’T ALWAYS RESISTANCE
People bring their history with them, and every job seeker, the experienced and the inexperienced, arrives carrying something. Some have experienced rejection. Some have been unemployed for a long time. Some have been told they aren’t capable; this is especially true for neurodiverse people and those experiencing physical disabilities. Some have had employers make assumptions about them. Some have been told what they should do their entire lives. All of this and more shapes their reality.
The point is that every person has a history, and that history influences how they respond to advice.
The key distinction is that understanding advice and trusting advice are two completely different things.
Someone can understand exactly what you’re suggesting and still not be ready to do it. That isn’t necessarily stubbornness. It may be fear. It may be self-protection. It may be previous experience. It may simply be that they believe “I’ve tried things before, and they didn’t work.”
PART III — WHAT IS THE RESISTANCE PROTECTING?
I used to spend hours wondering and asking myself about the resistance of my job seekers to my coaching. The question, “How can I overcome their resistance,” seemed unanswerable until I learned to change the question to “What is their resistance protecting?”
I have learned that maybe it protects their dignity, their independence, their confidence, maybe a fear of failure or sometimes success, maybe the fear of rejection, and even the belief that people like them don’t get those opportunities because of stigma, misinformation, trauma, and the impact of successive failure.
This changed my role.
I wasn’t fighting the person. I was trying to understand what the person is protecting. Success came when I started working with them rather than against them.
PART IV — THE CONTRADICTION OF “STANDING OUT”
I encourage and coach people to stand out, and that philosophy is in stark contrast to how many people have learned to survive in our world. Unintentionally, our school system doesn’t protect students from teasing and has a neurotypical bias that can push people who are different to the periphery and, as a consequence, conformity becomes the default. It is difficult to trust me to encourage them to stand out because almost everything in their lives reinforces not standing out.
The deeply ingrained conventional job-search wisdom is: Look online for jobs; use your prepared 1-page resume; send your resume; wait until the employer contacts you; if you are lucky enough to get an interview, attend the interview; wait; if they call you for the job, congratulations; if not, repeat.
I tell people they need to standout and challenge convention thinking, Look online for jobs as part of the multiple pronged job search that appreciates only 20-30% of jobs are posted online that includes referrals, direct outreach (Cold Calling); prepare a resume that could be 1-2 pages and shuffle your skills to match the job advertisement; credit a customized cover letter that uses the tool that is artificial intelligence with your own editing that creates a cover letter to match the specific job; find the name, position, and email address to send the application to the specific person in charge of hiring; follow up respectfully in 5 and then 10 days; prepare for the interview, create appropriate questions to ask the employers; follow up the interview; and even if unsuccessful, congratulate the employer when they give you the bad news, ask them to keep you in mind in case their choice doesn’t work out and ask them for their advice on what you could do better.
It’s a lot of work; nobody else asks them to do this.
This is the point of trust.
I tell them, “You need to stand out.” This is the how.
I encourage job seekers to break conventions, not because I am trying to be rebellious, and not because conventional wisdom is always wrong. It’s because conventional wisdom isn’t necessarily wisdom. Sometimes it’s simply repetition.
PART V — WHY BREAKING CONVENTION REQUIRES TRUST
Unconventional advice is scary. If someone has spent years believing there is a “right” way to find a job or has been told by other career advisors and reinforced by AI, and I ask them to step outside something familiar. I know they are thinking that’s risky.
I will often suggest contacting an employer before a position is posted; encourage building relationships rather than simply submitting applications; approaching someone inside the company; changing how they present themselves in appearance or in their narrative; I often use unconventional résumé strategies; using a employer problem-focuses interview approach; identifying something unique about themselves rather than hiding it; and always be looking for opportunities that aren’t sitting on a job board. This is different.
But from the job seeker’s perspective, I have learned they will be thinking: What if this doesn’t work?
That’s the question underneath the question. That’s where earning their trust comes in.
PART VI — THE ADVISOR HAS TO TAKE A RISK TOO
As a career advisor, I don’t pretend to have every answer. I listen and learn about what my job seekers want to do, and we begin. We try things, we see what works and doesn’t work; I tailor my approach to where they are, and often, when results aren’t forthcoming, we will try something different.
My willingness to experiment and challenge convention is never based on telling my job seekers to “Trust me. I know what I’m doing,” and I never ask anyone to blindly follow me. I invite them to be part of the process. I build trust by making them bring their own expertise into the conversation.
Their expertise is knowing themselves. I know employment. They know themselves.
The magic happens where those two things meet.
PART VII — GIVE PEOPLE BACK CONTROL
Rarely do I ever tell people what to do. I try to give them choices. Instead of saying, “You need to do this,” I will discuss with them setting some goals and ask them if they feel they can accomplish them. I don’t see this as lowering expectations. I see it as increasing ownership.
I believe there is a difference between helping someone do what I think is right and helping someone discover what they believe is right for themselves. My goal is to develop the skills people need to successfully find a job without needing me.
PART VIII — TRUST IS BUILT IN SMALL MOMENTS
Trust isn’t one conversation.
Trust is built when your job seekers see you do what you said you’d do; you remember something they told you weeks ago; when you don’t judge them when they don’t follow through; when you admit when you don’t know; when you tell the truth without humiliating them; you respect their “no”; you celebrate all of their small victories; you don’t disappear when things go badly; you allow them to make mistakes; and you listen before reaching for a solution.
Trust isn’t built by saying, “You can trust me.” It’s built by giving someone repeated reasons to discover that they can.
PART IX — DO WE TRUST THEM?
This is the important question nobody asks. Trust is a two-way process. As a career advisor, I constantly remind myself not to fall into the trap of believing I have all the answers. To be successful in helping them, I must trust them from our first meeting. I appreciate that they know things about themselves that I don’t; I trust that their hesitation contains information I need to listen to; I trust them and let them make mistakes; I let them define what success looks like; I try to stop rescuing them so they can learn. Trust isn’t one-directional.
You can’t ask someone to trust you while demonstrating that you don’t trust them.
PART X — TRUST DOESN’T MAKE PEOPLE MOVE FASTER
Trust makes movement possible. Every one of my job seekers has heard me say, “We work at your speed, not mine.” I can be ready for someone to apply for ten jobs. They may be ready for one. I often see possibilities they don’t yet see. I will know and believe they are capable long before they believe it themselves.
My job isn’t to drag them forward. My job is to walk beside them.
I don’t move people at the speed of my expectations. We move at the speed of their trust. Sometimes that’s fast. Sometimes it’s painfully slow. But slow movement is still movement.
PART XI — THE MOMENT THAT MATTERS
When a job seeker tells me, “I tried what we talked about.” This is the payoff. The job seeker tried the unconventional approach. Maybe it worked. Maybe it didn’t. Either way, something important happened. They tried. They took ownership. They stepped outside what was familiar. They trusted the process.
Perhaps most importantly: They trusted themselves enough to act. That’s the real success. It is never about proving that my advice was right.
PART XII — THE ENDING
Success is never binary. I don’t measure success only by whether a job seeker got the job. A job matters, obviously.
But a job search is a continuum of a dozen small steps. My work helps people to become more confident, more independent, more willing to question assumptions, and more capable of making their own decisions; then we have done something considerably larger than helping them submit an application.
Maybe the greatest measure of a career advisor isn’t how many people followed our advice. Maybe it’s how many people eventually became confident enough to make decisions without needing our advice, because the goal was never to create followers; it is always about helping some develop the skills to find employment and to trust themselves.
That’s why we move at the speed of trust.
My job isn’t to convince people to trust my advice. My job is to help them become confident enough to question advice, including mine.
I believe my job isn’t to show people the road. It’s to help them become brave enough to leave the road everyone else is travelling.
Paul