The Fine Line Between Honesty and Desperation In Your Job Search

mm Russ Finkelstein

I’m returning from another month of career coaching on the road. To my friends I refer to these marathons of empathy as “empathons”, because so much empathy is required, I’m becoming quite an empathy athlete.

This empathon included around 200 one-to-one sessions with people, having conversations about their work, and brought me to Miami, San Juan, Washington DC and New York City at the beginning and end of my trip.

Empathon conversations remind me about why the work I am doing at ClearlyNext is so important. Most of us don’t know how to figure out what we want to do next, or how to achieve it. The conversations I have with people often serve as inspiration to write about an issue.

One such dialogue occurred for me on this trip and continues to reverberate in my head as an under-discussed challenge in our job searches: How honest can we be, and with whom?

This conversation came to be as so many of mine do, a friend put me in touch with someone I knew from some professional circles, but not well. He had recently lost a very senior job at a prominent company. The job loss came suddenly as a result of restructuring, and now he was trying to figure out what to do next.

I should also share about him that he comes across as unflappable, determined and supremely confident. He has been taking regular meetings with his impressive network, as he looks for his next opportunity. We swapped the names of shared colleagues and opportunities that might be on the horizon.

We then moved to discuss things like:

  • What are the financial pressures you are facing and how long is your runway for a search?
  • What is your energy like for the search?
  • How are you managing this process, and by that, I mean: Do you have a plan, and how do you hold yourself accountable?
  • What are your goals from these conversations, and do you have a set of questions you use?

Here’s where things got tricky. My fault.

When I speak to fellow entrepreneurs and leaders of every stripe I often hear about the pressure to be amazing, or worthy of investment of resources. What they carry is this notion of having to be perfect and in control of their situation. However, when we search for work, we sometimes feel the need to wear the costume of the supremely confident to cover up our internal self-doubt of feeling very needy.

So, as we moved on in our conversation, we discussed the specific nature of some of his recent conversations. And it struck me that sometimes our need to get across an assured confidence gets in the way of getting people to committing, or feeling the need to commit, to us.

I know that appearing to have anxiety or self-doubt flies in the face of all conventional job search advice, but read on.

I asked what was going on with his job search. Because he’s someone accustomed to being taken seriously and in charge, and always very self aware and composed, it struck me that many of the people he was talking to might think, “Oh, he’s going to be fine”. In particular because that is how he opened his answer, with the words: “Oh, I’m going to be fine.”

I’m not saying that you should go in to an in-person conversation eyes red from crying, or looking as if you are bewildered about how you ended up in this situation.

Suffice to say I too am an, “Oh, they are going to be fine” guy in many situations. We all are, because our time and capacity to care is not a bottomless well.

Sometimes you are better served by telling someone you know in your network, that you have a decent amount of trust in, that you are a bit concerned about what job you will have next. It’s about how you get across that shared human experience of what it means to be unsure, in order to build a bit of a bridge.

Maybe, you have a strong sense of what you want to do—you better, if you want real help!—but are concerned that given your salary requirements, or age, perhaps, that finding that next role may be a slow process. You might say something like: “I know that the depth of my experience and reputation will help me land something great, but I am also too aware that X means that this may not happen quickly. Any help you can offer of opportunities I should know about or people I might speak to, would be fantastic.”

Many people get hit up all the time with requests for help. There are only a few ways to stand out, in a good way. The first often is a blood relationship, family by birth, or marriage. The second is a long-standing relationship, often from old friends from any part of your schooling, and perhaps work, where you will always be seen as a first priority. These are people to whom who can express an authentic need, without making someone live in fear of what you might do to their reputation if they get behind you.

It’s about walking that fine line between honesty and desperation. Clearly you’re still professional and accomplished. You’re doing things, and you’re making an effort. But you’re also being honest with people and saying, “I didn’t expect to be here at this point. I suppose none of us ever do, but I am doing all I can to find the next best fit for my talents. I’ve had promising conversations with X and Y, but these things are hard to predict. I hope you can keep your eyes and ears open for an opportunity that might be a good fit.”

In my coaching, I have a tendency of being more direct with people than most are accustomed to. So, when I offered this advice, for him to be a little more vulnerable in his networking conversations, he seemed perplexed.

I shared that if he appears confident and certain about the road ahead, people might not feel that he really needs their help. How to make that case for why they can be the tipping point?

Things you can say that are on the honest side of the line include: “I’ve not experienced this feeling before. It’s uncertain. I’m not sure.”

Things on the desperate side of the line include: “I won’t be able to pay my rent or mortgage soon.” People think of being a champion for someone as an assessment of their judgment of the talent of others and know that a faulty recommendation can come back to hurt them. Don’t give them a reason to think that you could be that person.

He asked me how much he could pay for my advice, and I said, “don’t worry about it. You’re in a place where you need help.”

He looked bewildered, as though he couldn’t believe someone would just offer help when it was needed. That was our breakthrough moment, I suspect, because perhaps that’s the crux of the issue, for me: To make yourself vulnerable in a tough job search is to also admit the possibility that people might want to help you without any incentive to do so. It’s counterintuitive to the subconscious lessons many of us are taught in our careers.

But we all need to try to foster an attitude of greater helpfulness if we’re to transform our professional cultures in America so that more of us are able to thrive. And with that, we can also feel more open to being vulnerable. It’s why we started ClearlyNext—to create a space, (behind the relative security of a paywall!)—where people can talk frankly about their career concerns and try to figure out what’s next.

In my professional life I have found that many people feel much more comfortable giving help than receiving it. If you are out of work, go out there and get more support. If you are in a good place now, don’t forget, we never know when the bottle will spin and point towards ourselves.

Let’s always aspire to be the person we wish we had in our lives when we were without work.

Russ Finkelstein is Managing Director of ClearlyNext, a guided online career program that helps people of all backgrounds and incomes figure out what to do next. Read more >