Dear Jordan,

I’ve had two instances in the past year that felt like I missed the mark in the opportunity to help my professional career, one of which was a one-and-done situation with an external partner, the other a start of a new relationship with a group of internal stakeholders.

Maybe you can help me. How do you recover from a bad first impression? CAN you?

Thank you,

Constantly Cringing

I get some version of this email just about every week. Literally every single person I know has first impressions they wish they could rewrite. I know I have a ton.

Mine, in no particular order, include:

  • The time I high-fived a partner at my law firm the first time we met, thinking it would make us instant bros (it didn’t)
  • The time I introduced myself to a friend’s boyfriend, even though we had already met before, after forgetting his name the first time (yes, it is possible to make a second bad first impression!)
  • The time I approached one of my broadcasting heroes at a conference and offered to help her book some new guests 60 seconds after meeting her (also the day I learned it’s possible to be presumptuously generous)
  • The time I accidentally used someone else’s name in the greeting of a cold email to a prospective marketing partner (a little mistake I like to call “autopilot copy-pasting”)

And dozens of other interactions that could have gone much, much better than they did.

We talk a lot on the show about how to make a great first impression — and for good reason.

The way people perceive us in our first interactions dictates a ton about whether the relationship will develop, how it will develop, and which experiences and opportunities will come of it. Part of our job is perfecting the impression we make on people, which is a skill in and of itself.

But in a world where first impressions don’t always go as planned, what can we do about less-than-stellar first meetings?

Should we just write them off, and give up any hope of having a successful relationship with the person in question?

Or should we try again, hoping to rewrite the impression we botched?

And if so, how do we recover from our missteps?

After years of working on this topic with clients (and in my own life), I’ve come to learn that first impressions are not quite as fixed as they seem.

In fact, not only is it possible to recover from rough first impressions, but they can actually serve to enhance a relationship — if we handle them correctly.

But first, we have to fully own the experience when it arises — which brings us to the first principle.

Accept a bad first impression.

When we stumble in a first impression, our first instinct is usually to minimize the encounter and suppress the memory. We do this to avoid the embarrassment and rumination that occur after a rough conversation. (An evolutionary obsession, no doubt, about our status in the “tribe.”) In reality, that instinct usually prolongs the discomfort, sending it deeper into our unconscious minds, where it it festers. To work on a bad first impression, we need to bring it to full consciousness.

We have to accept a bad first impression in order to move on from it.

So don’t excuse it. Don’t blame circumstances or context. Simply recognize that the interaction could have gone better, acknowledge the role you played in it, and allow any residual feelings to exist.

Those feelings are a sign that your first impression matters — which is an excellent reminder. Time will take care of the raw discomfort, but you can only extract a lesson if you embrace what went down.

One helpful step in this stage is discussing the encounter with other people. When we talk about our less-than-stellar moments — with trusted friends, colleagues, and so on — we do ourselves a couple big favors.

First, we minimize the shame around the story.

We don’t hide our embarrassment and allow it to isolate us. Instead, we explore it with other people, invite them to share their bad first impressions (or, if appropriate, ask them to), and remember that everyone has impressions they wish they could rewrite.

When we hide these encounters, we increase the shame and create another barrier to improvement. When we open up about those feelings, they lose their power.

Second, we grow from other people’s experiences.

I’ve learned a ton about rewriting first impressions by hearing how other people have dealt with them. When I acknowledge these moments openly, I usually end up hearing a lesson I can apply to my own life.

So the next time you’re discussing an impression with a friend, ask them about their experience. How did they handle a similar encounter? What did they do to recover (or fail to recover) from it? Can they create a model for you to follow? Can they offer you a piece of advice or strategy?

Accepting a bad first impression means allowing yourself to begin exactly where you are.

It also means being radically honest with yourself. This is where all growth begins.

The one massive upside to a rough encounter is that you can only go up from there. But in order to go up, you have to be willing to own your missteps. That’s the mindset of the student, which is essential for improving your impressions in general and the relationship in question in particular.

From there, you can begin to…

Rewrite the impression.

Some first impressions are random and relatively inconsequential (like meeting a random stranger at an airport bar in another state, for example). Other first impressions are deliberate and relatively important (like approaching a potential mentor at a conference).

The first kind of impression, of course, is easy to write off. The second kind of impression is harder to write off, and might be worth rewriting — assuming that rewriting it is possible.

Let’s assume that the impressions we’re talking about now are of the second variety — worth rewriting, and possible to rewrite.

After you acknowledge a bad impression to yourself, the next step is to acknowledge it with the other person.

Mallory, a talented floral designer, recently found herself working on this stage of the process.

During a walk-through of a charity fundraiser she was attending, she happened to meet the event planner, who was on the lookout for new floral designers to work with.

Impressed by what she saw, she launched into an excited commentary on the whole event, including some thoughts on how she would have arranged the flowers differently. It was only when she finished talking that she realized she had inadvertently suggested the flowers weren’t good enough, and that the whole aesthetic of the event needed work.

This wasn’t her intention, of course. It just came out that way. They exchanged information, but Mallory sensed she had compromised the relationship by sharing her opinion too openly, too soon.

Mallory cringed all the way home, trying to figure out what to do. She wanted to build the relationship, but sensed that she had blown it.

Finally, she decided to try to patch the impression.

The next day, she sent an email to the event planner. Below is the text of that email, with a few details redacted.

Hi [Planner],

It was lovely to meet you during the benefit walk-through yesterday. I hope the event was a big success, and in no small part due to how meticulously the space was designed. You and the team did an amazing job…

… Although I’m afraid I might have given you a very different impression during our walk-through!

Sometimes when I see a space so beautifully done, I get a little excited, and can’t help but geek out about how I would have approached a similar event myself. I realized on the drive home that I probably seemed to suggest that the flower arrangements weren’t good enough or something, which honestly couldn’t have been further from the truth. (Face, meet palm!) I was just having fun imagining my own designs, but I recognize that it might have come across as a dumb critique.

I apologize for that! I hope you can tell that I really love floral design and event planning, and that I get pretty inspired by seeing it done in new ways.

Also, I was thinking about what you said about pricing, and there’s a floral supplier I highly recommend with an amazing selection and competitive rates. We work with them all the time and they’re GREAT. If that would be helpful, I’d be happy to make an introduction. Just let me know!

Best,

Mallory

What I love about this email is that it managed to do a few crucial things at once — and all in the right order.

  • First, it fully acknowledged and owned the impression.
  • Second, it specifically explained and apologized for it.
  • Third, it rewrote the bad first impression by reframing the faux pas (the flower critique) as an unintended expression of something more meaningful (a real passion for design).
  • Finally, it ended with an appropriate act of generosity (the offer to make an introduction to a supplier) that gave the relationship room to blossom beyond the first encounter.

As it happened, Mallory didn’t hear back.

That stung a little bit, she told me, but she chalked it up to an important lesson and moved on. Which sometimes is the only option we have.

But then, three months later, she got a reply.

Not only had the planner read and appreciated her note at the time, but she needed some last-minute backup for an upcoming event, and she thought of Mallory. That was the first of many gigs they did together, and this time, their working relationship went off without a hitch.

Rewriting a first impression depends on forgiving yourself for the interaction, then leading with humility, self-awareness, faith and generosity.

Let’s unpack each of those concepts briefly, because they’re all essential.

Forgiveness is about acknowledging, owning and releasing how the interaction went down.

For many people, that’s the hardest part. But it’s critical. We can’t convince other people to give us a second shot unless we acknowledge that we need one. And we can’t move on emotionally from a bad first impression until we forgive ourselves for the mistake.

Humility and self-awareness are about acknowledging the blunder with the other person.

For some people, this is terrifying. But these are precisely the qualities that make other people want to give us a second shot, because self-awareness has a way of cutting through our more unattractive behaviors.

When we aren’t too proud to acknowledge a mistake, we basically say, “I know I messed up, and that was unfortunate, but hey — I can talk about it, and I want to talk about it, and that says something more important about me than that weird first impression.”

In most cases, those qualities eclipse the original faux pas. But we have to be willing to embody them.

Finally, faith and generosity do the heavy lifting of actually rewriting the first impression.

Faith is about trusting that the interaction can be rewritten — specifically, that the other person is willing to rewrite it.

Generosity, as we talk about all the time on the show, is about finding appropriate ways to create value for other people. It’s that generosity that sets the terms of the relationship anew. When we create a specific form of value, we say, “I want our relationship to develop past that first interaction, and to make that happen, I’d like to add something to your life.” Once again, that generosity usually overwrites the original impression.

If the person takes you up on it, then they are confirming the faith you had, and they’re meeting you in that act of generosity. Which is exactly what happened with Mallory and the event planner.

Of course, the details will change from interaction to interaction. But Mallory’s experience is an excellent template for how to rewrite a bad first impression.

Now, let’s dig into a few key topics that are important to understand in this phase.

When to Apologize

When does a bad first impression merit an actual apology, as opposed to a simple acknowledgment?

There’s no hard-and-fast rule, but a good guiding principle is whether the other person was injured in some way, or otherwise placed in an uncomfortable situation as a result of the encounter.

Mallory felt she had unwittingly thrown shade at the event planner’s design, which might have hurt her feelings, rubbed her the wrong way or disrespected the dynamics of their working relationship.

More importantly, in virtue of Mallory’s role in the encounter — junior designer, relative newcomer to the industry, prospective vendor/partner — she felt her misstep warranted an apology.

But if the same thing had gone down with someone unaffiliated with the event, an apology would probably have been unnecessary or inappropriate.

When is it not necessary to apologize?

In short, when the principles we discussed a moment ago — humility, self-awareness, and generosity — are enough to address and rewrite the impression.

In those cases, the apology is baked into a respectful admission of what went wrong. We call out what happened, and by doing so, we implicitly say “I’m sorry.” To apologize formally on top of that would be overkill, and might even work against us.

So as you navigate this stage, consider your relationship to the other person, the nature of the first impression, how much injury or discomfort it caused, and whether the terms of the relationship going forward depend on an actual apology.

In many cases, simply acknowledging the moment is enough. If the circumstances are unique, an apology might be in order. Use your insight and instinct to guide you, but always commit to being respectful and self-aware. These are the most important parts of any apology, implicit or explicit.

The Power of Humor

As you might have noticed, humor is one of the greatest tools in recovering from a bad first impression. Though Mallory’s letter was pretty earnest, it did have a couple winks in there, with the “face, meet palm” comment and the overall tone of casual friendliness.

Being able to laugh about a bad first impression, even a little bit, goes a long way in repairing it.

In my experience, the type of humor that works best here is self-deprecation combined with self-awareness — in other words, something that says, “I know I messed up, I’m able to laugh about it, and I’m hoping you are too so we can move on.”

That playfulness communicates that you not only have a grasp of how you presented yourself, but that you don’t take yourself — or the other person — too seriously to acknowledge it. It also communicates that you want to acknowledge it, without coming across as needy or aggro.

In some cases, this is just a matter of translating a standard recognition in a more humorous way.

For example, instead of saying “I’m sorry I gave you that unsolicited piece of advice,” you might say, “I felt like a know-it-all schmo when I tried to tell you what to do. It probably sounded like I was dropping the mic, but really I just got a little too excited about offering my help to someone. Hope it didn’t come across the wrong way — my bad! #selfawareness.”

There’s always a role for humor, even in an earnest apology. And the combination of the two has a powerful way of repairing a shaky first encounter.

The kind of humor that doesn’t usually work is a joke that subtly reinforces — or defends — the bad first impression.

For example, a message like, “Didn’t mean to put you in a weird spot when I told you how badly I want to work with you! Guess I’m just learning to be okay with going after the things I want!” might communicate some self-awareness, but it completely sidesteps the respectful recognition we’re going for at this stage. In effect, it’s a “joke” that says, “I know I messed up, and I’m going to call out my faux pas, but I’m going to do in a way that defends my questionable choice and tries to make you see my first impression in a more favorable light.”

In my experience, that approach usually backfires. If you’re going to rewrite a first impression, then commit to rewriting it. Rather than cast it in a new light, use humor to fully own it, comment on it, and move past it. That’s where a playful sensibility creates the best results.

Vulnerability

When you openly acknowledge a bad first impression, you also present yourself as a true human being to the other person. You no longer appear defensive or infallible. You aren’t trying to advocate or deflect. You’re just being honest, thoughtful and open to sharing all parts of yourself — including the rough first impression — with another person.

This is true vulnerability, and this is how you can actually use a rough first impression to your advantage.

Every bad first impression creates an opportunity for your authentic self to come through.

Elan, a high school friend of mine, once told me a story that opened my eyes to this principle.

Years ago, he paid several hundred dollars for a ticket to a major private-equity conference. A lifelong finance nerd, he was intent on landing a job on Wall Street, so he made the investment to learn from the brightest investors and meet some prospective employers — especially from the one hedge fund he admired the most.

As it happened, his conversation with a VP at his favorite firm did not go particularly well. He overplayed his eagerness, underplayed his credentials, geeked out a little too hard about some of his investment ideas, and generally came across as green and nervous. Even though the VP gave Elan his business card, he didn’t have high hopes for landing an interview.

Except that Elan had an intuitive grasp of the principles we’re talking about here.

In his follow-up email, he acknowledged the encounter — much like Mallory did — but included a few more sentences that made all the difference.

He mentioned how inspired he was by the conference, how overwhelmed he was by all the brilliant insights, and how grateful — and yes, a little intimidated — he was to chat with someone doing the work he wanted to do.

It was a dream come true, he said, and if he seemed a little intense, it was only because he was coming to terms with how much this industry meant to him. If the VP had any advice for breaking in, Elan signed off in his email, he’d love to hear it.

When Elan got a job offer from the fund a few months later, the VP told him that his email made all the difference.

What he saw in Elan at the conference was an uneasy candidate trying to worm his way into the fund.

What he saw from his email afterward, however, was a passionate kid still learning how to express his enthusiasm, a young person with enough self-awareness to recognize his weaknesses and enough drive to track down the people and information he needed to achieve his goals — both of which are critical for smart investing.

Here’s what I love about this story.

Elan’s email didn’t just rewrite the first impression. It used the first impression to share even more of himself with his future employer.

He regretted making a less-than-stellar first impression, but that impression actually gave him an opportunity to reveal other qualities — more personal ones — qualities that were meaningful to the industry and to the person in question.

In other words, he used his first impression to become more vulnerable.

And to the VP’s credit, he recognized how that vulnerability spoke to Elan’s character. He later became an informal mentor to Elan, and Elan has become a well-respected hedge fund analyst because of it.

Interestingly, many people with textbook “perfect” first impressions don’t manage to create this vulnerability.

They can navigate a first encounter without saying the wrong thing, but in managing the encounter so well, they can also fail to leave a strong impression. Meanwhile, a person who stumbles in a first encounter — and then vulnerably acknowledges the interaction later — can end up creating even more of an impact.

The difference, of course, is the degree of vulnerability they create.

When they try to rewrite the impression without getting personal and taking a risk — even just by virtue of writing an honest email in the first place — they usually fail to move past it.

But when they lean into that vulnerability, they often discover an opportunity hidden within the mistake. That opportunity is the chance to connect even more deeply. And that’s how vulnerability can transform a bad first impression.

When to Move On

As important as it is to rewrite an impression when necessary, it’s also important to recognize when to stop trying. If we don’t, we risk doing even more damage — to the other person and to our reputations — in addition to wasting precious time and energy.

It’s worth remembering that a bad first impression can stick for any number of reasons.

It might be because the other person isn’t interested in giving you another shot (a fact, by the way, that often says more about them than about you).

Or it might be because the first impression was simply too strong, and no amount of revision will fix it. (When this happens, it’s usually when there’s been an especially egregious error, explicit insult, high degree of inappropriateness, etc.)

Or it might just be because the other person is too busy, overwhelmed or disincentivized to reengage. (Perfectly normal and acceptable.)

Whatever the reason, there will always be some impressions you can’t recover from — and that’s okay.

At the end of the day, it takes two to tango here. You have to make a good-faith effort to rewrite an impression, and the other person has to be willing to let you. We can, and should, always try. But when we fail, then we must accept that there’s nothing left for us to do.

When a rough first impression can’t be rewritten, we need to trust that they ultimately shouldn’t be.

And what are we to do about the residual discomfort? What do we do with the regret, anxiety and self-loathing that often linger after a bad first impression we can’t fix? Do we just allow them to fester? Is that just the price way pay for trying to make things right and failing?

Luckily, the answer is no. Because even the bad first impressions we can’t fix still hold tremendous value.

Which brings us to our next principle.

Use the experience to perfect your first impression.

Ultimately, our job in life is to use our experiences — good and bad — to become the best possible version of ourselves. Inevitably, we’ll have to weather some less-than-perfect first impressions in order to nail our future ones. When we learn from these encounters, we extract important lessons, which then give those encounters new meaning.

Jacklyn, a newer listener of the show, recently wrote me about how she’s been using her conversational missteps to calibrate her approach. After beating herself up for years, she finally decided to reframe her imperfect first encounters as necessary learning opportunities.

These days, every time she stumbles in a first meeting, she dissects the exchange, figures out what she could have done or said better, and uses that insight to make the next first impression that much better.

But more than that, she explained, she’s begun exploring the underlying dynamics of those imperfect impressions.

At a recent dinner party, for example, she felt she had made a less-than-brilliant impression on a few of the other guests. The next day, she realized that her own insecurity about whether she “belonged” at the party had made her jittery and uncertain. She explored those feelings with a therapist and a couple trusted friends, and realized that she had no reason not to be at the party — she had simply adopted the unconscious assumption that she didn’t quite belong, which is a universal anxiety. This was the belief she needed to address in order to get better.

The next time she was invited to a party, she found herself subconsciously embracing that false assumption again. This time, though, she recognized it, made a choice to let it go before the party, and found herself making much more confident impressions with her new friends.

By analyzing the emotional underpinnings of her bad first impression — not just the surface — Jacklyn was able to address the deeper foundation of her experience. She also found new significance in all of her past conversations.

When we use bad first impressions to improve, we discover the meaning hidden in our mistakes.

Like Jacklyn, we find that the initial discomfort was a small price to pay for the enormous insights buried in our rough first impressions.

Which habits, body language and jokes could be improved?

Which thoughts and beliefs make it harder to connect with other people?

What aspects of our pitch, introduction or presentation need to be adjusted?

These are critical questions we can only answer when we struggle. The struggle kicks up the data we need to resolve them. Successful impressions rarely force us to take a close look at them. That’s why we need to fail from time to time.

The other benefit to learning from our bad first impressions is the importance of forgiveness.

To rewrite an encounter, we first need to accept it. And a key part of acceptance is forgiving ourselves for making the mistake in the first place — and permitting ourselves to use it to grow. The reward for that forgiveness is learning. And learning is how we get closer to nailing the next impression we have to make.

Which brings us to another important principle.

Invest in relationships, not impressions.

In our quest to recover from a bad first impression, we often end up obsessing over that first encounter. But if you really think about it, a first impression is not the most important thing in a relationship. The truly important thing is the relationship itself. A first impression is just a bridge that gets you from anonymity to connection. That’s it.

Jenna, a recent clients of ours, learned this by working on a rough first impression she had made on a partner at her environmental law firm. After working for months to charm him after a shaky first meeting, she was frustrated to find that their working relationship wasn’t getting any better.

So we decided to explore Jenna’s dynamic with this partner.

When I asked her how much concrete value she was creating for him — by helping out with cases, drumming up new business or creating new IP for the firm — she realized how much she had been fixated on how this partner saw her, rather than on how valuable she could become to him. By obsessing over his impression of her, she had forgotten the whole point of making a good impression in the first place: to build a meaningful and valuable relationship.

Jenna immediately refocused her efforts.

Instead of working on the charm offensive, she decided to focus only on adding value to the partner’s life by helping out on cases and assisting with business development. At the same time, she let go of how he “felt” about her — or rather, how Jenna felt he felt about her.

Six weeks later, she was surprised to find that their relationship has turned a corner. She had become one of his go-to associates, and her shaky first impression was just a distant memory.

(Not coincidentally, Jenna also said that her imposter syndrome improved significantly after that. Crazy, right? It’s important to recognize that the way we manage our impressions on other people actually has a profound effect on how we view ourselves.)

Once you move past an initial impression, your main job is to invest in the relationship in a generous and productive way.

This is exactly what Mallory did. Once she apologized for her faux pas, she confidently led with generosity, by offering to make an introduction to a supplier, paving the way for a productive working relationship. Jenna followed the same principle by focusing on concrete value rather than appearances. They both stopped fixating on a single impression, and decided instead to invest in the bigger picture.

How someone first perceives you, while important, is actually the least meaningful part of a relationship.

We don’t need to fixate on it more than is necessary. Beyond building that bridge toward a relationship, worrying about a first impression can easily become about narcissism and ego, rather than about developing meaningful connections. If the end game is the relationship itself, why not skip the middleman, and just start investing?

Because how you manage a relationship is far, far more important than how it begins.

So ask yourself:

How much value do you create for the other person?

How much do you lead with kindness and generosity?

What role do you play in each other’s lives?

Which values and qualities are you embodying in this relationship?

Are you working on being liked, or are you working on being worthy of the relationship?

These are the questions that dictate the quality of a relationship. Emotionally intelligent people understand that best. And by following this principle, you can teach others to understand it, too.

Which brings us to our final principle.

Calibrate your view of other people’s first impressions.

Armed with these techniques and mindsets, you’ll be in a much stronger position to recover from rough first impressions. But you’ll also find that you’re able to better judge other people’s first impressions on you.

Victoria, a school administrator, brought this to life in one of our workshops.

One of the surprising benefits of improving her first impression, she told the group, was how much more forgiving she had become of other people’s.

In fact, at the start of the workshop, she had met a fellow student who seemed nervous and uninterested. By the end of it, she realized that he was just exhibiting patterns she had too on a number of occasions. Normally she would have assumed that he was rude or untrustworthy. But now, Victoria just saw someone who might be having an off day or struggling with meeting new people.

By improving her own impressions, she made it easier for other people to perfect theirs.

We tend to have far more compassion for our own missteps than for other people’s. Part of our job is extending this awareness to the people we meet.

When other people fail to make a perfect first impression on us, we can choose to interpret it with empathy rather than judgment. We can give them the benefit of the doubt, refrain from making assumptions about their character, carry some of the weight of the conversation, or simply remember that they might be going through exactly the same experience we’ve gone through on multiple occasions. Most importantly, we can choose — if it makes sense — to give them another shot to form a relationship, just as we wish other people would do with us.

When we do, we invite those people to prove that they’re more than a single interaction — to actually build a relationship with us — which is ultimately a gift to ourselves as well as to them.

So yes, great first impressions are a key skill.

But it turns out they’re not the most important part of building a new relationship. The most part is giving the relationship the best possible odds of succeeding by investing in it with the right values and approaches. And oftentimes that means improving upon the first impression when it doesn’t go as well as we had hoped.

We can — and should — hone our first impressions as much as we can. But in a world where they don’t always land, we should also hone this secondary, and more important ability: the ability to accept and rewrite them, which turns out to be the key to even more meaningful relationships in the long term.

[Featured image by Yuri Levin]


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