Hi there, Lisa here. Before we start the show, I have a few disclaimers that I would like for you to keep in mind, as you listen to each Episode. First, this show will cover a variety of topics related to connection, mental health, work, & life; & some of these topics may be sensitive for you or someone you know. I want to offer you permission to choose courage over comfort when it comes to consuming sensitive content; & also, permission to respect your own limits when it comes to consuming this content which may be sensitive for you. I also need to indicate that while I am a licensed therapist, I am not your therapist. This show is not intended to be direct professional advice & you should not use this as a substitute for individualized, professional help. Lastly, while I can assure you that any of the coachable or teachable content I share will have demonstrated effectiveness – & are practices I use myself – I can also assure you that I am imperfect & there are times when I do not act as skillfully, as I would have liked. My goal is to act skillfully, most of the time; & I very much want that for you, too! Now, with that said, let’s start the show. 

Hello & welcome to Wired to Connect, the startup mental health podcast that keeps you going every week, with our easily digestible lessons, skills, & stories, that you can put into practice immediately. I’m your host, your coach, your teacher, Lisa Birnbaum; I’m also a social worker, a therapist, & the Co-Founder of Strengths Squared: a therapy, coaching, & consulting practice, for startup founders & their teams, that I started with my wife & Co-Founder in 2021. The learnings we are sharing here, come from a combination of the lived experiences of the startup founders & startup team members we’ve worked with over the years, from our own lived experiences, & from research-backed strategies, too. And we are so excited to be able to share these insights here, with all of you now. In today’s episode, we’ll be discussing 

. . . The Importance of Accurately Assessing Your Startup’s Culture. Today’s topic came about after recently consulting on a project with an EdTech Startup. Prior to COVID, this particular startup was pretty insistent on needing to have an in-person, office culture. They had maybe 1 or 2 employees that they made exceptions for & allowed them to be remote – I believe because they had relocated – but they certainly did not want this to become the norm. Obviously, the pandemic changed things, & now, they are trying to embrace truly being a distributed, remote-first, company. 

I sat down with the co-founders to assess the culture they built & to talk through the perks that were added, in effort to support their employees’ wellbeing. I then met with everyone else throughout the day – either individually or in small groups – to get their perspective on the culture & these perks. Unfortunately, there was a big disconnect between the co-founders’ & the exec. teams’ view of their culture & everyone else’s. 

I’m going to talk through exactly where the disconnect was, in today’s episode. I’ll also explain the recommendations I gave, so that – regardless of whether you are a startup founder yourself, or are on the exec. team, or are a startup employee – you can start applying these recommendations to your own situation. 

So much of this is interconnected. I’m going to break all of this down for you in today’s episode. So, let’s get into it; let’s make some meaningful connections!

Support for today’s show comes from our very own, Strengths Squared. What if you really knew the type of startup founder you are, or the type of future-startup founder you are likely to become? Would it change your trajectory? Would you do anything differently? Well now you can better answer these questions for yourself, by taking the quiz we created, specifically for startup founders and future-startup founders. In 10, pinpoint questions, you’ll identify your leadership strengths, as well as your opportunities for growth. At the end, you’ll see which type of startup founder you are – or which type of future-startup founder you are likely to become – so that you can move forward with the clarity, courage, and confidence to ensure that your type is working for you, rather than against you. Just head to: strengthssquared.com/quiz to take the first step toward being the best startup founder you can be. That’s s-t-r-e-n-g-t-h-s-s-q-u-a-r-e-d-dot-com-forward-slash-quiz, and we can’t wait to hear which type of startup founder you are! 

Today’s episode is an inside look at my recent consulting project with an EdTech Startup. They went from previously, being heavily steeped in their in-person, office culture; to now, learning the ins & outs of being a distributed, remote-first, company. After meeting with the co-founders, and all of their employees, it was clear there was a big disconnect between the co-founders’ & the exec. teams’ view of their company’s culture & everyone else’s. 

I’m going to take you through this disconnect so that you can better understand how it surfaced. 

Let me start with the areas of alignment, though – the places where everyone was generally on the same page – to help provide you with some context: These co-founders did a really nice job pivoting their offerings during the pandemic; an excellent job transitioning to a distributed, remote-first culture; & relatively speaking, they haven’t had a tremendous amount of turnover. They’ve embraced asynchronous communications, they refined their onboarding so that the experience is meant to happen virtually, & they upped their game with the new swag they’re sending to new hires & periodic surprise deliveries they’re sending to everyone, too. They also did a nice job rolling out wellbeing perks – such as reimbursements for things related to both, physical health & mental health – updating their parental leave policy & switching over to unlimited PTO. 

The areas of non-alignment and points of disconnect seemed to have a common theme: While the exec. team pointed to these wellbeing perks to show that their culture supported work-life balance; everyone who was not on the exec. team agreed that these wellbeing perks sounded good in theory, but that in practice, they missed the mark. When I dug into that a bit more, it made so much sense. In conversation after conversation, it became clear that – in spite of the changes made during the pandemic – what was being reinforced was an always-on, never-not-working, hustle culture. And that in order for folks to feel able to take advantage of these perks, they would need to have: 

• sufficient time available – outside of time spent either on work or thinking about work – to actually use these perks; 

They would need to have:

• their co-founders & their leaders modeling for them, the fact that they are using these perks; & 

They would also need to have:

• their co-founders & their leaders encouraging them to actually use them, too.

It also became clear that a number of folks not on the exec. team felt disconnected from one another & believed that their opinions on the direction of their product were not valued. When I dug into these a bit more, it became clear that – even though they like the distributed, remote-first culture that’s emerging – they also miss the non-work, in-person connection. In a number of conversations I had throughout the day, I also heard how most decisions at this company – including those related to product direction – were made in a very top-down way; & it became clear that folks not on the exec. team wanted to be included, wanted to feel heard, & wanted their opinions valued.  

After spending the day meeting with everyone, – & after helping them understand the importance of rest, recovery, & down-time – I gave some initial recommendations to the co-founders & the exec. team, as well as some initial recommendations to those not on the exec. team. 

First, I recommended the co-founders & the exec. team start by realigning their expectations around asynchronous communication, by clearly communicating those expectations to each team, & by ensuring that each individual team member understands these expectations. 

I then recommended the co-founders & the exec. team, each sit down with their calendars over the next few days & block out a certain number of weeks – out of the next 52 weeks – that they will commit to taking off from work. I recommended at least one week per quarter, plus one extra day each month, in addition to the full parental leave for anyone that applied to. And, I recommended identifying this time openly on their calendars. 

Next, I recommended the co-founders & the exec. team choose one way they could each commit to investing in their physical health & one way they could each commit to investing in their mental health; & seek reimbursement for both, using the process they had in place. For any of them who identified difficulty turning off, difficulty spending time either not on work or not thinking about work, & difficulty buying into anything other than hustle culture, I recommended therapy specifically, to work on these & to prevent burnout. Regardless of how each of them committed to investing in both their physical health & their mental health, though, I again recommended they each identify these ongoing times, openly on their calendars. 

I also recommended the co-founders & the exec. team find ways to include prioritization of time off, physical health & mental health into everyone’s OKRs; so that these are the behaviors that get reinforced – rather than the always-on, never-not-working, hustle culture behaviors that were inadvertently reinforced, previously – & so there’s no question that the co-founders & the exec. team want everyone to actually utilize these perks. 

I then recommended the co-founders & the exec. team start to facilitate some in-person connection, in the form of twice yearly company retreats & monthly get-togethers to attend based on location; as well as some more frequent non-work connection, in the form of a weekly activity done together virtually. 

The last of my initial recommendations for the co-founders & the exec. team was to rethink their weekly Exec. Team Meeting & to consider including everyone else – in small groups, on a rotating basis – to this meeting. I explained that by providing folks not on the exec. team an opportunity to hear what’s being discussed & by inviting them to voice their opinions – depending of course on how this is executed – these hopefully serve to chip away at the power imbalance, & enable them to feel included, heard, & valued. 

And, after effectively adopting each of these recommendations, I also encouraged the co-founders & the exec. team to then socialize these recommendations among everyone else. 

As for those not on the exec. team, I recommended starting to experiment with setting limits & boundaries around their working & non-working hours. I explained that ultimately, they were given an opportunity to work whatever hours they want to work, & that they can actually set some limits & boundaries around this. I also confirmed that, previously, when they’ve been available & ready to respond to requests at any time, they have actually inadvertently reinforced their co-founders’ & exec. team’s propensity to continue making these requests. 

I further clarified that this meant, deciding for themselves, the 30-40 hours per week they would like to devote to work; & then, practicing self-discipline by not engaging with work outside of those 30-40 hours. I recommended they reflect on & consider how they could start to implement this. 

I also recommended they take some time now, to think about how they would want to use their wellbeing perks – the reimbursements for things related to physical health & mental health, the updated parental leave policy (if applicable), & the unlimited PTO – so that once they see their co-founders & their leaders modeling the utilization of these perks, & once they experience their co-founders & leaders encouraging the utilization of these perks, the decisions about “where to start” have already been made. 

The last of my initial recommendations for the folks not on the exec. team was to attend the in-person & remote gatherings, as well as the newly formatted Exec. Team Meetings – as often as possible – & to practice the mindfulness skill of non-judgment, by going into each with an open mind & an open heart.  

As I hope you’ve come to appreciate, so much of this is interconnected. I’ll be back to recap all of these connections, right after this …   

Support for today’s show comes from our very own Strengths Squared, a therapy, coaching, and consulting practice, partnering with startup founders & startup teams. At Strengths Squared, our goal is not to have to treat burnout after the fact; and instead, to prevent burnout from happening in the first place. We do this by equipping startup founders and their teams with the necessary skills to build sustainable, mentally healthy work cultures of collective care, collective accountability, & intentional work-life integration. If you are a startup founder, a startup team member, or are someone who might be a future-startup founder, and are navigating a challenging topic that you would like addressed on our show, or you have a question you would like answered on our show, please send an email to: podcast@strengthssquared.com for a chance to have your topic addressed or to have your question answered, on a future episode. Again, that’s p-o-d-c-a-s-t-@-s-t-r-e-n-g-t-h-s-s-q-u-a-r-e-d-dot-com, and we’ll keep our eyes out for your topics & your questions. 

Let’s go ahead and pull all these connections together. To recap, my 6 suggestions for giving feedback, effectively are: 

Let’s go ahead & pull all these connections together. To recap, after spending the day meeting with everyone, – & after helping them understand the importance of rest, recovery, & down-time – I gave some initial recommendations to the co-founders & the exec. team, as well as some initial recommendations to those not on the exec. team. 

For the co-founders & the exec. team I had 7 initial recommendations:

1. Realign expectations around asynchronous communication, clearly communicate those expectations to each team, & ensure that each individual team member understands these expectations.
2. Commit to blocking out time taken off from work for the entire year; of at least one week per quarter, plus one extra day each month, the full parental leave when applicable; & identify this time openly on calendars. 
3. Commit to one way of investing in physical health & one way of investing in mental health; seek reimbursement for both; & identify these ongoing times, openly on calendars. 
4. Determine how to include the prioritization of time off, physical health, & mental health into everyone’s OKRs.
5. Plan for in-person, twice yearly company retreats, & in-person, monthly get-togethers; as well as non-work, weekly activities done together virtually. 
6. Reformat their weekly Exec. Team Meeting to include everyone in small groups, on a rotating basis. And, 
7. Socialize these recommendations among everyone else. 

Now for the folks not on the exec. team, I had 4 initial recommendations:

1. Decide which 30-40 hours per week to devote to working hours & experiment setting limits & boundaries around working & non-working hours.
2. Practice self-discipline by not engaging with work outside of those 30-40 hours & reflect on & consider how to start implementing this. 
3. Think through & decide on ways to utilize the new wellbeing perks so that the decisions about “where to start” have already been made. And, 
4. Attend the in-person & remote gatherings, as well as the newly formatted Exec. Team Meetings – as often as possible – & practice the mindfulness skill of non-judgment, by going into each with an open mind & an open heart.  

Thank you so much for listening to today’s Episode of Wired to Connect & I hope this was helpful. If you’ve got a question, you would like answered on our show, just send an email to podcast@strengthssquared.com – that’s p-o-d-c-a-s-t@s-t-r-e-n-g-t-h-s-s-q-u-a-r-e-d.com – or use the link in the Show Notes. And, if you would like a chance to win a Free Startup Coaching Session, which retails for $500, keep your ears out in the very next section for-the-instructions.

That wraps up today’s episode. I hope you loved it! Don’t forget to hit “Subscribe” or “Follow” on your favorite podcast app, so you don’t miss an episode. And, we are currently giving away our Free Startup Coaching Session! If you want to win a free coaching session, just leave us a rating & write a review on Apple Podcasts or the podcast app of your choice; and you’ll be entered in our weekly, random, draw. This type of startup coaching session retails for $500, & can be yours for free; by rating and writing a review of our podcast. Then, listen in next week to see if you won. It’s that simple! Thanks so much in advance, for supporting us on Apple Podcasts or on the podcast app of your choice!

Before I go, I want to leave you with this: After assessing this EdTech’s culture, the biggest concern for me was actually not the disconnect between the co-founders’ & the exec. teams’ view of their culture & everyone else’s view of their culture. The biggest concern for me was that the folks not on the exec. team were telling me all about this disconnect, rather than telling their co-founders & their execs. directly! I spoke with them at length about this – so I’m not sharing anything here that I haven’t already shared with them or anything they haven’t okay’d me sharing – & I think it’s important to note here, too, that in order for those not on the exec. team to have felt okay voicing their concerns, there needed to be a level of psychological safety. And, unfortunately, that psychological safety did not exist. Psych. safety is an immensely important topic, so I’m going to devote our next episode entirely to that.   

Okay, I think that’s it for me, for today. Be sure to tune-in to our next Episode, Episode 11, which will be all about Psychological Safety. Can’t wait to connect with you then!

Thank you to my incredibly talented cousin, Andrew Fisher, for writing & playing the original music for this show. And, from the bottom of my heart, thank you to my amazing wife, partner, & Co-Founder, Marisa, for your belief in me, & in this show; for everything you do for our family & for Strengths Squared, for everything you are doing behind the scenes for Wired to Connect, & without whom, none of this would be possible! Lastly, & perhaps most importantly, thank you so much, to all of you who are listening, for supporting us by choosing to spend your time with us, for connecting with us, & for keeping an open mind & an open heart. I’ll look forward to connecting with you in next week’s episode. And until then, take good care, & remember, we are all Wired to Connect!