Good news
I just started a new role as a delivery coach, helping teams adopt a new way of working. It is great to be paid to do work I love again.
Looking for a job is the opposite of that. Obviously, you are not paid, but it also turns out to be a lot of work, and a lot of it is work I don’t love.
Since I love coaching people and helping them adopt better ways of working, I have been reflecting on whether that applies to coaching myself when I am “not working.”
Some reflection or a PIR
If you know me, then you know I enjoy reflection. But ironically when I coach I also warn of the dangers in doing that.
Often the best way to improve how we work is to start working and then improve, rather than over-analysing all the complexity without acting, which often turns into a form or procrastination or delay.
In that spirit, the best way to get better at “not working” is to start looking for work rather than overthinking how to do it or putting it off.
So a good “ways of not working” coach would probably help me get started, rather than using analysis as a form of procrastination before starting, as I might be prone to do.
Getting started
Strangely, Claude and Gemini helped me a lot with getting started, though not through any form of coaching. Instead, using AI reduced the complexity and procrastination of the first steps, after which I found I could stay focused until I was done.
I like to start with the end in mind, though—what is the problem at hand, what is the outcome I would like to see, and then what do I do to close the gap? Great in theory, but the outcome of each job application is generally to get rejected. And that is not really the vision I want to focus on.
“Rejected” is not a nice word, and perhaps I could say I was “unsuccessful at this time but good on me for trying” or something nicer, but “rejected” is in fact a concrete and accurate description.
The WOW “way of not working”
Applying for jobs is really a sales activity, and I have always said I would not like to be a salesperson. One of the reasons is that good salespeople have real grit; they know every closed deal sits on a mountain of failed attempts. That puts me off starting but it is what good salespeople seem to be able to turn into motivation.
That is a mindset I respect, and I wonder if it is core to someone’s personality or something that can be developed through coaching and practice. Either way, it involves leaning into the expectation that you will face rejection and that you will be strong enough to keep going until you succeed.
I found that being rejected was actually not as bad as the word implies. The fear of rejection is generally worse than the event itself. Kind of like procrastination is harder mentally than action, worrying is harder than the actual experience of rejection.
Perhaps thinking like a salesperson helped. I was pitching my product (which in this case is me), and pitching is a process rather than a one-off event. Treating it as a numbers game, I tracked applications made per week, conversion to first interview, and then each other step.
Tracking numbers gives me a sense of progress and makes things less emotional, but more importantly, it keeps me focused on the actual outcome and what I can refine to get there. I recommend setting up a sales funnel and, like some geek, tracking things like applications made, coffees consumed with friends, or screening interviews reached. You won’t need to report to anyone, but it seems to help me focus and might be good for you too.
The art of rejection
Sometimes I was rejected very politely by people who said I was great and that they gave my application careful consideration, but that they had a lot of applications and someone was a better fit.
There seemed to be quite a lot of that – a lot of politeness but not a lot of empathy in the process. But at least the rejection email served its purpose well and I was clear that it was the end of the process.
More often, though, I needed to infer the rejection after an appropriate period of silence. Sarcastically, I could suggest that the complexity of setting up an automated reply was not worth the investment to just reject people, so the value of the application people made was less than the time it would have taken.
Anyway, after two weeks, I could assume the role was filled because I found that if I did not hear back in that time, I would not hear back. I could pretty much flag it as unsuccessful and forget about it. A good salesperson would follow up, but I found that in many cases there was nobody to reach out to, or they would not respond. In one case, the person was no longer working there anyway, so I guess they had turnover or outdated content in the job ad.
Either way, the most frequent outcome was a concrete or inferred rejection. It might be gentler to say people “rejected my application” rather than saying that they rejected me personally. After all, it was the application they saw, or that AI culled automatically, that was the basis for the decision; they did not know the real me.
While that is true, and probably the way I would frame it if I was mentoring someone, I find on reflection that it is a little more nuanced when it is me and my application being reviewed.
The essence of rejection
The resume and cover letter were how I decided to represent myself, and so the rejection was of that—the me I showed people. Of course, the me I showed an AI algorithm was a 1-2 page summary of one aspect of my life, at a high level.
But applying for a role still involves a choice about how you represent that information, based on the audience and what you want them to think of you.
And if there is useful reflection on how to improve, then the essence of what you communicated about yourself when you got rejected, is a good place to start.
I did not find the rejection painful, but actually something I could learn from, if there was any actual feedback to use in learning.
Limited feedback to learn from
Unfortunately there was generally no useful feedback to learn from. That is fair enough when an algorithm is matching data, or someone only has an application letter to review and has to compare it to 100 others.
One organisation was different in that they literally summarised how I went in each interview and gave me feedback, which was really useful and also something I am grateful for.
But in that case I was in 2 interviews and they had more to give feedback on.
The art of being rejected
I would have predicted that the rejections of the applications I put a lot of effort into would sting the most.
Surprisingly, they didn’t. Perhaps the rejections for roles I really thought I was a good match for had more sting than others, but even then it was only fleeting. Perhaps thinking of the process as a funnel of opportunities helped. I think it would have been a lot worse if there was one long application which was make-or-break.
I would like to put a positive spin on it by saying that at least I learned from each rejection, but again this turned out not to be the case. I did learn that the few remaining Agile roles are now “SAFe Certification strongly preferred” and that change management roles seem to be based on knowing a specific process, rather than demonstrating driving an outcome, based on the ads. But mostly, the polite rejections offered little concrete feedback to learn from.
Interestingly, though, the process of putting applications together did provide more learning than I expected.
Learning without feedback
Breaking years of complex work into a limited number of bullet points is painful, but the act of doing so revealed a lot of highlights I had forgotten about.
Again Claude helped with this. With each role I asked for a match and for gaps in that match and Claude did two useful things:
- It reminded me of things that I had added to other applications or interview debriefs that turned out to be relevant; and
- It highlighted apparent gaps where I actually had tackled problems that were not mentioned in my resume.
So it was generally the process of applying for roles that created the learning and not the upfront thinking I did or the feedback I got.
The art of good rejection
Occasionally, though, I did receive an authentic and even positive rejection. I could share these, but I don’t think you could cut and paste the content to make your rejections better, because they were authentic to the organisation’s culture rather than clever or “best practice” templates.
They were not even personalised or specifically written for me, just well-written based on empathetic thinking.
One was from a charity that supports mental health by providing information and experiences in building resilience rather than responding to a crisis, and their rejection showed that they authentically believe in that. Not only did they provide further steps and information if I wanted to be more resilient, but they also worded the email in a way that seemed to recognize how I might or might not feel, while avoiding being patronizing or smarmy.
The other was a small charity that matches volunteers with young people who want mentoring or support to improve their lives. I was probably not the right match for them in the role they had, so they rejected my application. But they also used the opportunity to pitch the idea that I could still volunteer for them.
That might seem cheeky, and I don’t recommend you pitch your company’s products to people as you reject their application. But in this case, their job ad had emphasized that the benefit of working there was the ability to make a dent in the world. It was actually consistent with their initial message. Since what appealed to me about the role was the chance to make a difference, the suggestion was an actionable next step if I wanted to take it.
The agency created by empathy
I did not decide to donate or volunteer for either organisation, but both rejections left me thinking about the value of their organisation and gave me a sense of having a choice to do more.
I have put a task in my diary to consider whether I have time to volunteer next year after I focus on settling into a new role and sorting out some other things.
So both rejections actually improved their brand for me and left me with a feeling of agency. That is quite an achievement when rejecting someone’s request to come an work with you.
My conclusion
So what can I take away from all that?
The way rejections are framed by the one rejecting someone, and the one getting rejected, makes a significant difference to the experience.
The work of looking for a job almost always involves a lot of rejections, just like a salesperson managing unsuccessful leads. You could put more into every lead and maybe you should – I found a lot of advice on LinkedIn to do that in different ways.
But I found it incredibly useful to frame things as a funnel of leads moving through multiple decision points or stage gates.
Looking analytically at the “way of not working” was really helpful once I got started.
Next time I am “working at finding work”, I will repeat this process: get started first, then improve the system and the content. That includes building a book of “stories” or “STAR based Scenarios” and the other content as well as the way I manage my work.
Maybe that is good advice for others, or maybe it is just what I enjoy, but either way, it is exactly how I will do it next time.
