Confidence and humility are not mutually exclusive

As I meet entrepreneurs seeking to launch their first startup, I’ve begun noticing behavioral traits I wasn’t paying much attention to before.

Signals I’m picking up more frequently are from entrepreneurs coming across as super confident (even aggressive), perhaps in an effort to show they are hard driving and ambitious.

While confidence in one’s beliefs is indeed a critical asset for a startup entrepreneur, my BS detector begins kicking in when I see a total absence of humility. The tells are things like:

– working their accomplishments into the conversation
– no hint of what they don’t yet know or are seeking to learn
– expressing no curiosity about whom they’re interacting with
– interactions appear motivated only by potential self interest – no evidence of “pay it forward”
– how they interact with others who serve or bump into them seems different than their style of interacting with those in a professional context

Because I’m an investor who looks hard at leadership qualities of the CEOs I want to work with, my mind gravitates towards thinking: “If this is what I’m noticing now, I wonder how it translates to future interactions this entrepreneur has with others they seek to recruit and lead?”

Humility as a leadership trait

If you’re looking for thoughtful insights backing up the quality of humility in leaders, check out Jim Collins’ Good To Great and his work profiling Level V leaders. His research supports the thesis that CEOs embodying the unusual combination of fierce resolve and personal humility ended up being a critical leadership trait for top performing companies in the study.

My own view was shaped most by my Dad and my wife Krista, but also the good fortune of having close contact with a bunch of exceptionally strong leaders who personify humility in how they lead and interact with whomever they meet.

Jack Stack, Founder/CEO of SRC and visionary behind the Great Game of Business would certainly top my list in exemplifying resolute commitment and personal humility. SRC is not only a phenomenally successful company that has transformed thousands of lives, but beyond Jack’s Southern gentleman’s humble style, his open sourcing of the GGOB and open book management practices empower a generation of entrepreneurs like me to embrace principles around getting everyone in a company to think and act like owners – the ultimate management humility as it means running an organization with the power bubbling from the bottom up.

Back in 1995, Anthony Martin, now retired Chairman/CEO of global staffing giant Select (and subsequently Vedior) picked TriNet to invest as one of the 40+ companies in his portfolio. Much to my benefit, he traveled “across the pond” for 10+ years to sit on TriNet’s Board of Directors. Soft spoken with never a wasted word, his gracious, gentle, almost patrician manner helped set the tone for our board meetings with wisdom that came through penetrating observations and questions that were so much more effective than the contrasting style of boards featuring competition to demonstrate who is the smartest guy in the room.

In the emerging tech world, anyone that knows or interacts with uber VC Brad Feld (@bfeld) will attest he gives so much of himself to so many causes (building entrepreneurial ecosystems, women in tech, computer science education and entrepreneurship globally to name just a few) and notwithstanding an incredibly packed and productive schedule and contact list, still shows an uncommon curiosity and willingness to pay it forward with each new person he bumps into.

Humble, super successful people stand out

So I take notice when I encounter a super successful person who isn’t showing the expected trait of being the center of attention in a dialogue among a small group.

My respect grows as they instead show curiosity in others and demonstrate care and concern for people they don’t know, as well as how they contribute talent towards things not driven by self interest.

Encounters like these also reinforce my not losing sight of humility in what I say and do.

Paying it forward is going to be a theme I hope to keep shining more light on. Not only to help keep me centered, but also my belief that raising awareness of success beyond financial measures is the real story behind entrepreneurs with the most impact.

Reap Serendipity From Creative Collisions

Since what we accomplish is often linked to who we meet, first time entrepreneurs are particularly motivated to extend their network for new relationships leading to partners, customers, team members and capital sources to name just a few.

But even with a wish list of possible relationship needs, it’s not practical to jump into every group or event we see or blindly flail about without a plan increasing odds of success in locating and interacting with those we are looking to meet.

That probably begins with figuring out where the richest environments might be – not only with the densest population of our targets, but also connectors that might lead to the high impact sources we’re seeking.

As an example, since most VC’s depend on referrals from trusted sources as their primary source of new deal flow, it’s worth thinking about who supporters are in the ecosystem like the right service providers, angel investors and other referring sources who can be more easily accessed through networks and group events.

High value in meeting new people face to face

A surprising number of millennials I meet seem hesitant to put much time and effort into building their network by regularly pursuing higher volume of face to face interactions with people or groups they don’t yet know.

The comfort of working the keyboard to troll through social networks and existing connections seems more time efficient – to which I respond “Keep doing whatever is working for you – but if you’re not yet finding the people you want help from, maybe it’s time to mix in some traditional methods of how most new relationships get started.”

We know that when we first meet someone face to face, we’re likely to follow social norms with a courteous dialogue that subtly has each person checking the other out. Both parties arrive at their respective conclusions with a lot of intuition and non verbal clues that simply can’t come across in email or an online profile.

With even a brief interaction, we’ll generally know whether we’ve been able to generate the needed spark of interest with whom we’re talking to – thus guiding us towards which of the people we just met will get some follow up attention.

And since some of the strangers we meet turn out to be givers who want to help, the human dynamic of meeting them in person stimulates curiosity and dialogue that may result in offers that would have been very hard to stimulate from a direct “cold call” or digital approach to that same person.

You give before you get

People who haven’t done business in Silicon Valley are generally surprised to hear the ethos of “pay it forward” is what truly powers startups there. The ease at which first time entrepreneurs are able to both find and access so many of the right givers is the essential glue that makes it the most entrepreneur supportive environment on the planet.

And giving is not limited to just those who are already advanced in their professional journey or accomplishment. If you’re the person seeking help, you have a chance to show your stuff and surprise someone by figuring out some small give to a person you just met and don’t know well yet.

Even if it’s just a small nugget of info that is on target with that person, being proactive in giving sets you up for being memorable and perhaps starting a new relationship instead of a forgotten interaction of no value to either party.

Can’t predict what comes downstream

When I peel back the history of some of my most life changing relationships, a surprising number can be traced back to origins from unanticipated creative collisions.

A majority of the initial interactions were with people who in turn introduced me to the high impact investor, partner, customer or team member not present at the event where I met the connector.

Other people on a young team might have roles less dependent on securing high impact external relationships. But for the founder/CEO in an emerging company, expanding the relationship network is a sufficiently high impact activity to justify being an ongoing part of the schedule.

Even though some events and groups won’t pan out as productive exercises, the ones that do will yield results to make all the difference in the journey.

Related post: Building Relationship Capital

Building Relationship Capital

With a big chunk of my time devoted to accelerating Upstate NY’s startup ecosystem, I think a lot about how starting new relationships is critical to making a successful startup community.

The ease in which strangers can drop into a place like Silicon Valley and meet the right people is a dynamic that outsiders aspire to, but don’t seem to put much energy towards figuring out in second and third tier markets like ours.

So among other initiatives, I’ve been playing up the importance of building relationship capital when I’m interacting with first time entrepreneurs who are usually pretty light when it comes to the relationship network they need to build a company.

Relationship impact may not be obvious at initial interaction

Any entrepreneur who has built a serious company will have their own stories about key people they met along the way who ended up having a significant impact on their success, yet their initial interaction seemed fortuitous.

In contrast, I’m seeing a lot of first time entrepreneurs focus maniacally on pursuing relationships they perceive will lead to capital, but with too narrow a focus that puts them at risk of overlooking others who might be possible mentors, advisors and referral sources. These are the relationships that eventually lead to capital providers, customers, channel partners or other highly prized relationships vital for a startup’s success.

A person I just met might open one door, many or none but I won’t know what will unfold until a relationship deepens over time. That means planting lots of seeds, nurturing the right first time interactions into relationships – especially with people having a mix of capability and interest in advancing a dialogue.

Relationship Capital Fueled By Being Proactive & Crossing Boundaries

Figuring out who to meet has never been easier. In this transparent world with such readily accessible information about people in business, how hard is it to come with a top 10 list of people that would be good to know, or the intel on who their friends are or where they hang out?

Supplementing a targeted list of people would be organizations/groups and events populated by people likely to include the profile of those having some things in common with your interests.

Again, a bit of research is needed – just don’t fall into the common trap of thinking that the only relevant groups are those somewhere within immediate view such as your university, local area or industry.

Developing high impact relationships are well worth the time to invest in targeting, crossing boundaries to new organizations and even traveling as needed to interact with a group of like minded others to tap into new networks and forge new relationships.

You give before you get

The principle of reciprocity captures the essence of what it takes to turn a chance encounter into the first stages of what could become a productive relationship.

Think about the casual interactions you might have at a reception event. In these settings, the most successful people I know are naturally curious and usually not the ones opening up unless questioned by others. Instead they query you about your interests, often times subtly honing in on the areas where they might possibly be able to help you.

Can you uncover something in your dialogue to offer up (even if at a later time) to that successful person asking you these questions?

Once you know more about the other person, your give might be a relevant article or post you came across, a recommended place or event or best of all – an introduction to someone else or a resource that you’ve figured out would be helpful to who you’re talking with.

Being Systematic

Planting lots of seeds and nurturing a whole bunch of recent contacts into productive relationships takes work that most people won’t do. Those who are truly connectors are organized with disciplined contact management and calendaring of follow ups.

In the TriNet world of referral generated sales, we learned to get highly systematic in building processes around keeping our reps constantly identifying and nurturing their top relationships – a foundational element of our building a referral based culture and company.

More recently, that systematic approach to relationship building is incorporated into IntroNet – an app which helps people connect others and track what happens with the introductions they make.

Any one of these relationship development tactics would produce some results in helping meet and come to know more people who could help you.

Put them together and you’ll be on your way towards achieving that next big thing, no matter what that might be.