leadershipmanagementpersonal development

Scale Yourself, Know Yourself

In September I was asked to participate in the PACT Capital Conference “Lion’s Den”, a Shark Tank-style event in Philly. The conference bears the distinction of being the oldest and most established conference connecting VC, PE and entrepreneurs in the Northeast. (Right on, Dean Miller.)

In preparing the conference materials, they asked me for a quote for the attending entrepreneurs to accompany my bio and adult-ish headshot (lolz).

I offered:

It’s just as important to scale yourself as it is to scale your team, but remember to be strategic about it! Double down on your strengths and hire complementarily for your weaknesses – but before you do either, make sure you invest the time to really know yourself!

I’ve written a lot about personal growth, scaling myself and scaling the team in the past (here, here, here). These are the post-revenue things for a startup founder and they represented a disproportionate amount of my time at RevZilla.

Remember, we didn’t spend a ton of time or money to discover or invent a new market in moto – we set out to redefine the eCommerce experience through scalable tech and media.

Simply said, we took execution risk (vs. market risk) in launching RevZilla with the goal of becoming the “Zappos of Motorcycle gear.” We believed if we could build it without burning through all of our personal savings, we were 85% sure we’d be a leap ahead of what already existed in the industry.

So we holed up and built for six months pre-launch and within 90 days post-launch the site was cash flow positive. I have only appreciated that more and more as time has passed. Being involved in a ton of VC-backed companies these days, it feels like we skipped half the founder work of fundraising and managing investors.

BUT – we still had to execute and executing is all about the team. With that, we can bridge back to the critical “know yourself” part of my quote above. I still believe it is the foundational aspect of scaling yourself, your team and your company effectively.

“Knowing yourself” is the output of an ecosystem full of data points about you that comes from many angles and places. Some are self-serve from within, but most of the really valuable ones come from others – if they trust you and care about you enough to share.

Here are some of my learnings and maxims that helped me mine my personal ecosystem for the necessary truths needed to scale my impact, i.e. become a better leader:

React Consistently – If people trust you and feel safe, they may actually give you true feedback. If you get crickets a lot, even when you ask directly, they are scared of your reaction and what the consequences of sharing may be. If you react consistently to bad news and constructive feedback, even when you don’t agree with it, you train people to know that the messenger is never in danger. Your actions need to match the words.

I once had C-suite member offer in the most diplomatically way possible that I “at times was a hair loquacious in meetings”. If he felt safer, he would have told me, “Booch, you are sucking the air out of the room in meetings and it may be impacting the ability to have the most valuable and fully participated conversations”. And he probably would have told me 6 months before I formally asked, as well. Also if he didn’t feel safe offering it to me even when I asked, there is no way more junior folks felt safe enough to offer suggestions for ways I might support them better. I was happy I learned this lesson when I did, but wished I had learned it years earlier. From there on, I consciously worked to be more predictable. If they know you will react in a safe manner, even to rough or personal news, you may be surprised in how useful the things you start hearing will be.

Feedback is a Gift – Now that people hopefully trust that you will react reasonably, continue to ask for and show gratitude for feedback. Seek it constantly – informally and formally – from individuals, small group settings and in your town halls, if possible. When people care enough about you to share how you could improve, they are spending cycles for you and sticking their neck out on some level. Never forget to thank them for it and reinforce your appreciation.

I read once that the only good direct response to any piece of feedback from a peer or subordinate should be “thank you so much for telling me that”. You can always follow up for more clarity and texture later, but in the moment when folks are uneasy about your potential reaction, put the person who’s sharing back at ease. Reward and reinforce their effort to help you and the organization improve and train them to do more of it in the future. Wanna bet they tell their co-workers how you reacted? You have just modeled great behavior that could affect their managerial interactions downstream, as well.

Feedback is a Gift Part 2: No Real-Time Examples – You have now offered immediate gratitude to the party who has attempted to help you, right? From there you can talk about a lot of related things, problem-solve together and you can certainly hope that the sharing party gives you some specific examples backing up their perceptions right then and there. In my experience, the odds are low that you’ll get specific examples with the initial feedback. Sometimes you’ll get full texture from more experienced and comfortable feedback givers which I’d consider a bonus. But, no matter how flimsy or concrete the sentiment being shared, you never get to ask for examples in that meeting. In the sharing context, asking for examples is the equivalent of saying “I won’t believe you unless you prove it right now” and it supports the fear / consequences aspect of speaking truth to power.

As I mentioned earlier, you can always find a moment in your next interaction to get the extra clarity you need, but the patience not to ask immediately will reinforce the feedback loop and eliminate future fear. Sidenote – Conversely if you are sharing any negative feedback or area for improvement with anyone you should ALWAYS have multiple examples to create as much clarity in the moment, as possible. Take the guesswork out where you can. Highlight the cost element being addressed.

Feedback is a Gift 3: Advertise your Plan – After you have processed the feedback, gotten any additional clarity and potentially thought through how to change your approach in the future, advertise your new approach to the person brave enough to have shared the feedback with you originally. Remind them that you appreciated it, and showcase that you heard them and that you found value in their opinion. The ultimate testament is actually modifying your behavior when future opportunities present themselves.

Leverage the Friday 5:15 – The “5:15” is a weekly “post” shared with you by someone you manage within a document that they own. It’s not a progress report, it’s another scalable feedback loop to be used in supporting the individuals on your team. Generally, it’s completed every Friday by 5:15. It should take a staff member 15 minutes to write and five minutes for you to read.

Done well, it’s short and specific, giving you a sense of where your teammate’s head is at as they wrap up the week along with highlighting anything new they may need from you ahead of their next 1o1. My promise was that I’d have read and potentially commented back by Monday at 9am, so long as they were completed on time. At RevZilla we tested these in the exec ranks and found them valuable enough to be rolled out company-wide. There is more to the concept and you can find a broader article and my podcast discussion on the topic here. In my eyes, a scalable tool supporting servant leadership from a schedule perpetually under fire.

Share Your Defaults and Preferences – I’m a D9I8S1C5 on the DISC profile. I’m an ENTJ/P in the Meyers Briggs matrix. I’m a Challenger-Enthusiast (8/7) on the Enneagram spectrum. I prefer collaborative problem solving and I would prefer bad news delivered in person during specific work blocks vs. via electronic means. I have even more communication preferences on a number of common scenarios as well.

During my career, I have shared my information in a mixture of places but never pulled it all together. I’ve seen others who I respect collect and build a 1-2 page “Operating Manual” with all relevant preferences and links. They then shared their personality, work and communication styles manual with their team in an effort to help them find more success and consistency in their interactions.

Next time, I will centralize my data and share it via the extended “operating manual” approach. If (when) I received feedback that the team found the document valuable, I’d then ask them to create a manual for their respective teams and I’d look to be shared on it, as well. As a manager, I obviously try to use all the tools at my disposal to understand my people.

It’s worth noting that some folks don’t put much stock in personality profiling. In my view, a personality profile is just another framework for simplifying a person’s inherent needs and patterns that affect communication style, which is the true productivity unlock here.

Learn the Other People Patterns – So many of the same people patterns have been distilled in a number of different flavors across many books and articles. A committed 3-6 months of regular reading can build a heck of a leadership foundation. One truth spans all of the following resources: It’s all people, the higher you climb, and the person it starts with is yourself. Some of my favorite written resources: What Got You Here Won’t Get You There, The Hard Thing About Hard Things, Principles, Any Number of First Round Review Articles on Management or Culture, Trillion Dollar Coach, Reboot.

Avoid the Vacuum – The climb is way harder alone. Find other climbers. Get out of your office and invest in building your network of folks who sit in a similar seat, at a similar stage of company or personal life. Compare notes on the self-development journey. Their perspectives may help highlight things you have not already thought about, along with identifying red herrings or shortcuts to less obvious solves. This one is so trite, but I see so many founders who live in their own echo chambers or, worse, celebrate not playing well with others.

Find Grey Hair Who Can’t Fire You – This is in the same vein as the last bullet, but rather than peers, find a mentor or an exec coach. I’ve written about it before, but you need to discuss what scares the hell out of you with someone you’re not married to and who is not on your cap table or payroll. Even more importantly, that person should know you and care enough about you to be able to call bullsh*t when needed and without fear of repercussion. When you have someone in your corner who sees enough of your patterns and has a non-financial stake in your outcomes, they can force intellectual honesty and, hopefully, highlight additional blind spots for you to work on.

You can always be better. More effective, more supportive, more introspective, more efficient. Don’t ever let yourself, your management style or your approach to leadership be “done”. Grind your way to excellent.

Make sure that you are getting strong regular signals from your feedback loops and personal ecosystem that you can act on. Make it part of your management framework. Share your approach with your team and help them make it part of theirs.

Think about the compounding effect if all of your managers and leaders got better at scaling themselves and their leadership by only 5% each year. Think about what it might look like if the output of the effort were that your company improved all its KPIs by 5%. #mindblown

As I said, feedback is a valuable gift at the foundation of scaling success on all fronts.

Never settle.

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