The More Senior You Are, The Longer the Job Search
All names and personal details have been changed.
Madeleine* was feeling incredibly frustrated. “When I was in my twenties, I could get a new job in a month! Why is it so much harder now? I have so much more experience, I’m more senior, I’ve worked for incredible companies, done wow-worthy work, it’s nuts that this is taking so long!”
Sound familiar?
It seems counter-intuitive, but all that seniority, experience, credibility that would make you assume things would move faster is actually what slows you down!
Or there was Diego* who had a massive network from his business school days. “Everyone is doing better than me and making all these relationships and announcing these huge promotions. I’m being left behind and these are my biggest years to earn!”
He did have a massive network, he just didn’t know what to do with it. That along with some green envy was getting in his way!
There was Jolene* who found that she was constantly getting bombarded with potential opportunities, and the annoyed that none of them panned out or fit her needs.
She was relying on inbound, instead of focusing on her desires and going outbound.
Most of the folks I work with are seasoned professionals. They’ve been working for 10, 20, sometimes 30+ years.
They’ve built incredible careers.
They’ve led massive teams. Impressive programs. Created beautiful things for big-name brands.
And their job hunt is inching along at the pace of a snail and feels like one massive hurdle.
Completely different than when they were in their twenties and could land a job within months, sometimes even weeks!
Why?!
I’ll tell you!
Why is the job search so much harder and longer for more established professionals, seasoned workers, and senior leaders?
We’re pickier. We may have been able to get a new gig in weeks, but, we’d never take that role now! Now that we’ve become more seasoned in our career we have more opinions and requirements about what we want. We (hopefully) know what types of roles we’d accept, the companies that interest us, the industries that are enticing. We have more restrictions around titling, salary, benefits packages, location, etc. This is a good thing. Twenty-five year old Rikki did some wild things at work - I wouldn’t want the gigs she took then now!
Our lives are more complex. When we’re in our twenties, most of us only have ourselves to handle, maybe a fur baby and rent to make. But as we become more established, we need more specific things to support the changes in our life. We may need to be able to leave early for school pick-up, easy remote work days for surprise sick kids or being able to travel to an aging parent. We may want to be able to travel less - or travel with family! Whatever the complexity is, our pickiness is increased and impacted.
There is more competition for less roles. Most organizational structures look like a mountain. Roles for early career are plenty. But they slowly ladder up and there are less roles the more senior you go. So where there may have been 20 designers at a company, there’s 8 senior designers, 3 design leads, and only 1 VP. (Or whatever, insert your ladder stuff here) That means that there are less roles at your level, and, more people going for them. So it’s going to take longer to find your way in.
The interview process is more complicated. For a designer, if we’re hiring 20 - we just grab ‘em! But for a design lead, or a VP - they have significant impact on the team, the vision, the strategy. We can’t do two to three quick rounds of interviews. We need more time to assess them from a top-down (and bottom-up!) approach to ensure they can fit well with senior stakeholders, cross-functional team members, and direct reports. Many more people have to sign off, and, because we’re getting paid more - we also need to demonstrate additional expertise to ensure we’re the right fit! Otherwise we - and them- could make an incredibly costly and time-intensive mistake in a hire!
Companies are pickier, too. Those 20 designers? Totally fine to have several that went to the same school, or came from the same company. But as we move up the chain, the company themselves have more opinions. You may be a “perfect fit” because you’ve done this exact work at a competitor. But, the company wants new, fresh ideas - not borrowing from what’s already out there. Suddenly all that perfect fit expertise is working against you. Insane, right?! Or, you may be a great culture fit and background, but of the three design leads, someone already has that background and the company wants to diversify their senior leadership. Oh well, they got there first.
Their networks aren’t thinking of them. We have massive, established networks. But we don’t know how and when to use them. No one is reaching out to us anymore. That’s because… they’re not thinking of us! They assume with our impressive backgrounds and titles that we’ve got it all sorted out. We actually have to reach out to them, keep them up to date, ask them for specific things, etc. It’s not that they don’t want to help. It’s that they don’t think you need any help. And, they’re busy! So go reach out. And then reach out again when they miss that first note/text/email.
They’ve forgotten how to search! The job market changes over time. Previously, if a designer’s resume wasn’t visually stunning, it was a no-go. Now, most designers need both a visually pleasing resume, and, a simple text resume to get it past the AI screeners that are combing through hundreds of applications. Product managers used to go in and tell a simple story. Now, they look ridiculous unless they’re quietly following the STAR format. Someone who earlier in their career could apply directly to a role, interview, and get it is so established now that they have to work with senior leadership to craft the role based on the company’s needs and their abilities. Simply put, as we become more senior, more established, the job hunt is much more complex. It requires a mixed approach between applications, networking, all that good stuff.
So now that you know they why it’s so much harder, we can’t just leave it at that. Let’s consider how to combat it.
What to do as a senior job searcher
Get clear on your wants and no-gos. This ever-changing list will help you assess if a role or recruiter call is actually enticing, or just exciting to be reached out to. It can help generate keywords to search for, organizations you’re interested in, etc. etc → I do an extended version of this with my career coaching clients called the Ice Cream Sundae (not trademarked but don’t you dare steal it!) Reach out to work together and we can make your perfect sweet cold dessert dish!
Go learn what’s out there. Roles, titles, companies, they all blur together. Go have conversations, informally, to better understand the landscape - and, how you fit into it! This can also revise some of your wants and no-gos based on those chats. In addition, these conversations can help you better understand the roles that don’t exist yet, or, help you pitch that you should join an organization based on their needs and your unique skillset. Write your own job description.
Prep your background and story goal. We get caught up in having the perfect resume, or wanting an elevator pitch that encompasses everything we want. It helps to create a three-sentence pitch that simply states: what you’ve been known for, what you’re looking for, and how they can help. That’s it. You can have different versions for different occasions: whether you’re at a wedding, networking event, or chatting at a bookstore.
Ask for help. They have no idea that you need or want help. This is so hard to do when you have an established network - you feel that people come to you for help, and it’s a sign of weakness to ask for yourself. That’s silly! Because you’re so senior, no one thinks you need help. So ask. Do it. They want to help. Adam Grant talks all about how people are primed and seasoned to help and they feel good when asked. So go help them feel good! Get clear on what you’re asking (i.e. Steps 1-3!) and go for it.
Be patient. The search will take longer for you (because of everything stated above) so take your time, and take care of yourself. Focus on how you can best support your mental, physical and emotional state while you go on this marathon. It’s not a sprint. So we’re going to need snacks, water, and stretch breaks.
Want a buddy as you work through this rollercoaster? Reach out.
I work with established professionals who are reimagining their relationship with work - whether that’s leveling up, pivoting, creating their own thing, or somewhere in between. We discover what’s important to them, take action, and get comfortable playing along that edge of growth and challenge. Oh, and we laugh a lot. I’m not very serious.