Unlocking the power of imperfection: Embrace your inner imposter!

Recently I had the privilege to be a keynote speaker at the Mind the Product conference in San Francisco. My topic was the Importance of Psychological Safety for Remote Teams. After introducing myself, I shared that even though I’m up on the stage, I have times where I feel like I'm an imposter.

After outing myself, I put a question to the audience - who else has experienced imposter syndrome? Lots of hands went up. Then I asked everyone to introduce themselves to the person next to them and share snippets of their imposter syndrome journey - when do they feel like an imposter, is there a trigger or situation which resonates the most?

After a few minutes, I brought the audience back together and asked the same question again - who else has experienced imposter syndrome? Even more hands went up. I wasn’t surprised as I truly believe the following statistic.

Throughout my career, I’ve found product people experience imposter syndrome more than other professions as we tend to be generalists interacting in a world full of specialists. As product people, we are often building something new and figuring it out as we go.  That can be over whelming and lead to wondering if I'm doing the right thing, in the right way, at the right time.  And, if I'm not, how long until someone else figures it out? To put it another way, being a product person means that by definition you're living in a world where no one knows the right answer yet because if somebody did, they would've already built it. 

Maybe then I shouldn’t have been surprised when a majority of the keynote speakers also mentioned imposter syndrome during their talks. It wasn’t planned. It just happened that way. I wondered what it was, why now, that so many of us are feeling a bit out of sorts. When I spoke with other speakers afterwards, a few put forward post-Covid and the current economic situation. We’re still feeling burnt out, and now so many jobs are at risk. These two factors are putting anxiety on high alert. [If you’re leading a team through this time, check out my post on the importance of psychological safety.]

How do you feel? Are there times when you feel like an imposter? If so, celebrate - yes, celebrate! For the egg above, turn that frown upside down ;-)

Why celebrate? Imposter syndrome and FUD (fear, uncertainty, and doubt) can be the “grit” that creates the pearl. Grit, as defined in Angela Duckworth’s Grit, the Power of Passion and Perseverance, is “perseverance and passion for long-term goals”. In product management, we are constantly navigating ambiguity and exploring unknown territory. Grit is what powers leaders - people who set their sights on a goal and then work diligently and intelligently to attain it. 

Today, in our rapidly changing product world, we are constantly trying out the new and unfamiliar as we look to bring delight to our customers. Always exploring the unknown is exciting and scary - and can lead to imposter syndrome.  So realize you're not alone. Instead encourage your team and yourself  to tackle unknowns and to quote Barry O'Reilly - get comfortable being uncomfortable. You’ll be amazed at what you can accomplish! Keep reading to learn from other talks.

Creating courageous product teams

Near the end of the day at Mind the Product, Yi-Wei Ang, the CPO at talabat took the stage. After his talk, a friend sitting next to me said, “I would hire him on the spot”. Yi-Wei’s words were that powerful. Why? Because he didn’t pretend to be perfect. He didn’t pretend to have all the answers. Instead, he dispelled the myth that product leaders are expected to have clarity and conviction even in the face of deep unknowns. Yi-Wei countered with “we don't know yet, we are trying to figure it out.” +1 for the truth.

To rewind, Yi-Wei began his talk by paraphrasing Brene Brown and sharing “the best products come from teams that make courageous bets.” His points being:

• If you are not willing to fail, you cannot innovate

• If you are not willing to build a vulnerable culture, you cannot create

To expand: Creating something new requires taking unconventional bets and acknowledging nothing is 100% certain (especially in product management). To take bets, you don’t need to have all the answers. Instead you can unpack the questions together (as a product team). This simple act of admitting to not having all the answers takes courage. It takes courage to be wrong; it takes courage to pull the plug and put aside an idea or retire a product; and, it takes courage to build a culture that allows for the vulnerability to try. It's a long journey that starts with you.

Here are the tips Yi-Wei shared for creating a courageous product team.

• At the individual level

  • Check your ego

  • Build the vulnerability muscle

  • Be curious not cynical

• At the organization level

  • Acknowledge it's ok to be imperfect as long as it gets better over time

  • Model authentic vulnerability (learn, share, grow together)

  • Lean into the difficult feelings in the room (never leave things unsaid)

    • Ex. share "fail of the month" and unpack the learning

    • Ex. you are not going to feel 100% certain of decisions, and that is ok

• At the culture level

  • Courage is contagious

  • When you embrace the struggle, you'll gain the individual and collective wisdom that makes courage your culture

  • When a culture of courage is built, work will never be the same again as a culture that embraces vulnerability enables your organization to rise to the top

Lessons learned from leading product teams

The last speaker of the day was Natalia Williams, the CPO of Hootsuite. Her talk was like a music countdown. For each of her points, she would play a corresponding song and have the audience guess the artist. The approach was incredible, and she rocked it! Despite the energy, Natalia also admitted she wasn’t perfect. She too makes mistakes.

When I teach my course on People-First Product Leadership, and after my talk at Mind the Product, people ask if individual contributors change the culture at their organization? I say “yes”. Natalia also believes you can change the culture at any level of the organization. Her guidance is by being empathetic with your customers, team, and with yourself, you encourage others to learn from both wins and losses. You can be the catalyst which sparks a culture of trust and respect.

Self awareness was another powerful theme for Natalia. She recommended the audience take both success and failure to heart, especially to learn from our own mistakes - going so far as to say that '“being self aware separates good from great product managers”.

Other points from Natalia’s talk that stood out to me were:

1. Admit to making mistakes

2. Acknowledge it’s not all about me (song: "we don't need another hero by Tina Turner")

3. Be open to feedback

4. Bring your team along in the journey

5. Invite others into the conversation (product manager super power - strong ideas, loosely held)

6. Embrace change as change is a constant; be comfortable in the discomfort of change

7. Change the culture by championing the change and bringing others along on the journey (it takes a village). 

8. Acknowledge as a product manager, my job is to come into shit on my desk every day and figure out how to get it off (I wish I wrote down the song for this one)

9. Start high cadence communication, there is no such thing as over communication

10. Agree on what a good product manager should be doing in your org, make the expectations clear and understood

The magic of thinking big

I’m a fan of Lenny’s newsletter and Lenny’s podcast. When going through my Mind the Product notes, I noticed I also had a write-up from Lenny’s talk at Mind the Product in July 2021. He started with the following quote.

Given what Lenny has achieved, there must be some power in his statement. The same belief went into the work he did optimizing the booking funnel at Airbnb. He shared in 2012, 50% of bookings were rejected. At the time of his talk in 2021, over 85% of booking requests were successful. The key, he said, was to “look at things as they can be, not as they are.”

At the start, the Airbnb team ran a whole bunch of small experiments over a six month period. Their efforts increased booking acceptance rates from 50 to 55%. Nice, but not the impact they were seeking. The team took a step back and decided to think big - specifically to imagine the ideal experience… a goal of 100% of bookings being instant bookings as instant bookings had higher acceptance rates. Internally people were uncomfortable and feared hosts would leave the platform. Instead of stopping, the team did the following:

1. Address internal concerns - hear people out, use data, run experiments, over communicate, bring on an exec sponsor

2. Determine an approach - think small and tactically (think big is for the vision, not the experiments)

The rest of his talk focused on point 2, specifically breaking down the problem from where the team ultimately wanted to land (e.g. 100% instant bookings).

• Identify what are the inputs (and levers for the inputs) that inform the metric you are trying to move

• Map out current state of the world (%) against the levers

• Identify the lever with the lowest level of discomfort and experiment —> which turned out to be host adoption, as new hosts didn’t know differently and could be presented with instant bookings being the norm

Guess what, over time the “new” hosts become the existing hosts. And, as the new hosts grew, so did the booking requests. Over time, instant bookings went from 5% to 60% of existing bookings.

All their efforts were not perfect. They made mistakes. For example, they tried an experiment which only allowed instant bookings. It went terribly. This learning led them to revise their goal form 100%, and go with 80% being the new definition of “success”. Yet, they would never have reached the 80% if they hadn’t thought big from the start.

Key takeaways:

1. Think big when tackling a big opportunity

2. Imagine the ideal experience and work backwards

3. Break it down

4. Think small when executing (with a sprinkle of big bets)

5. Jump ahead to the end state to see how far you have to go and revise your goal, if necessary

Enjoy!