Monthly Archives: February 2016

Building, Nurturing, & Sustaining a Culture of Organizational Trust

Images via Bossfight.

Developing an organization where trust is a fundamental part of the bedrock isn’t something that anyone in their right mind would balk at. I mean, it kind of goes without saying, right? A healthy organization is one where trust is the very lifeblood.

Consequently, there’s not a single business owner who would intentionally seek to create a business that would even be considered close to the opposite, especially when they first start out.

Yet, over a period of time (depending on how quickly the erosion may occur) we begin the see the wheels of these organizations come off — and it can all begin to point back to the bedrock. This is what I mean specifically when I talk about “organizational debt” and the consequences of allowing accrual to happen for too long.

Unfortunately, for many leaders, it catches them completely off-guard: “What happened? Where did it all go wrong? Who’s to blame? Is there blame to give? How do we stop it from ever happening?

At this point it may be too hard to recover, or at least without significant reconstructive surgery or an entire reboot, and no one wants that.


The disappointment leaves us feeling alone, isolated, abandoned.

We all know what it likes to be disappointed by the people that we love and respect, the people that are closest to us. Heck, it may have happened this past week as someone personal (or professional) totally let you down.

Herein lies the framework upon which true organizational trust sits upon — the key is first understanding this very critical and fundamental principle is the reality that people will disappoint and the gap of expectations that we all may have:

Occasionally, there are gaps between what we expect people to do and what they actually do.

Read that over a few times and tell me that you can’t think of 1,000 examples of this in your own life. These experiences might include colleagues, friends, parents, business parters, your girlfriend / boyfriend, your spouse or partner, your boss. The list goes on-and-on, right?

These gaps have the propensity to show up at any moment (and typically at the “wrong” time). In fact, you might be battling with some of them at this very moment. You are faced with making some critical (and emotional) decisions about what you want to do with your time, your effort, your relationships, your career, and perhaps even your life as a whole. It sounds melodramatic but we know that it’s not — it’s real life.

Part of your decision-making process has been related to these gaps, the expectations that you had for others that have not yet (or were never?) met. These gaps have created a rift that you are not entirely sure is solvable, a chasm that you’re not entirely sure you can navigate and cross.

But here lies an unbelievable opportunity:

We get to choose what goes in those gaps.

We have the opportunity and responsibility to choose what goes in those gaps. We can either:

  1. Choose to believe the best.
  2. Choose to believe the worst.

Obviously, the first of those things is easier said than done. Choosing to believe the best about people is tough. Sometimes, it feels dangerous. Sometimes it feels unfair.

Choosing to believe the best about someone requires sacrifice and is not often returned “in kind” which can, unfortunately, lead to even more heartbreak and sadness.

But there’s always hope.


Real friendship is risky — it always will be.

Like most things in life there is always an upside, if we have the courage to look for it. Nothing ventured, nothing gained, right? Think, for a moment, about the best friends that you have and the reasons that you became great friends with them.

Let’s take it to another level, shall we? Think upon the person that you decided to partner with for that really cool startup idea. Think about the person that you decided to marry.

You opted to believe the best about who they were and your expectations about them. You did, in fact, sacrifice a lot so that those relationships could flourish and thrive. You decided (you intentionally made a decision) to trust them. You chose to believe the best instead of defaulting towards the worst.

But then things suddenly changed, things shifted, the ground that you felt was so rock-solid now feels like quicksand and in the worst of times you may even feel like you’ve made a terrible decision about them.

Here’s the opportunity! You and I get to choose what goes in that gap, remember? We have the power to choose.

But it’s so hard (I know, I know)! “You don’t know what they’ve done to me!” Yes, yes, I get it. I know. “They said they would but they didn’t!” Yup, been there, experienced that. “It hurts, I should have known better!” I guess, but could you have really known better? Are you clairvoyant?

There are two elements to this new equation that must be sussed out and those two parts are as follows:

  1. What I see (them do, act, behave).
  2. Who I am (and my responsibility).

What you see (or think you see) now is different than what you expected you would see when you first started. The way that person handle decisions, or the way they interact with you or your clients or customers or partners. Perhaps it’s the way they handle money or accounting and financial matters. Perhaps it’s the way they spend their time (or what you believe them to be doing with their time which might be contrary to what you see).

In essence, you have begun to doubt the integrity of that person, you begin to doubt what you perceive to be true and all of these things that you observe have caused you to question the person’s sincerity, which, consequently, has created a significant gap in your expectation(s). You are flirting with the idea that they may not be trustworthy; you are might even have already landed there.

But just as important is the fact that you also have an vital and critical part to play in the dynamic. Who you are as a person has created a bias (neither good nor bad, mind you, but a real bias and perspective) which has and will continue to influence your thoughts around these matters.

So you have to consider your own point of view and ask yourself the hard questions surrounding the context of some of the gaps that you may be seeing or experiencing. These aren’t comfortable questions, mind you, but they must be asked:

  1. How much of the gap has been part of your own making?
  2. Has the gap been created in conjunction with some of your own perspectives, biases, assumptions?
  3. What is your part to play?

Like any relationship, as they say, it’s a “two-way street” — pithy and perhaps trite, I know, but, it doesn’t make it any less true.

Developing a culture of trust is critical to the health and success of any organization and to do that you must be willing to encounter and engage with these difficult questions at all levels of the organization.

You see, a healthy work / relationship environment all the time with every single person is not realistic (although we almost naively believe it’s possible and we expect that it will happen).

The bottom-line is that trust fuels productivity, in any size organization, and a culture characterized by trust attracts trustworthy people and quickly surfaces those who are not.

Two corollary truths:

  1. You will never know who you can’t trust until you trust them.
  2. You will never know who you can trust until you trust them.

I think Jim Collins has said it best when he once said:

The moment you feel the need to tightly manage someone, you might have made a hiring mistake.

Don’t take this as gospel and I think the most important consideration is the “might have” in his statement. The point is that you don’t know until you know and to figure it out you have to encounter, ask, and investigate.

It’s your decision on how (and what) you put in that gap.


It takes real work to build a culture of trust.

Five Commitments to Close Expectation Gaps

To move forward productively there are a few commitments that individuals and the organization can commit to so that trust is maintained and that productivity remains high.

These are simple, straight-forward, and very actionable:

  1. When there is a gap between what I expected and what I experienced, I will choose to believe the best.
  2. When other people assume the worst about you, I will come to your defense.
  3. If what I experience begins to erode my trust, I will come directly to you about it.
  4. When I’m convinced I will not be able to deliver on a promise, I will inform you ahead of time.
  5. When you confront me about the gaps I’ve created, I will tell you the truth.

Take a moment to marinate on those for a bit of time — they are easy to read but difficult to digest and even more difficult to actually practice.

The best relationships that you have have these elements already embedded deeply within them — you just may never have qualified them as explicitly as I have here.

And you’ve probably been through a few of these scenarios before: You’ve been told that a friend of yours is acting “strange” (“different” or “out of line”). You defend your friend and you choose to believe the very best. But, when you begin to observe discrepancies, you went to them and asked them about it. And, your relationship was strong enough to have an honest conversation about the topic at hand.

Pretty great, right? This dynamic can and should happen at both the personal level and the professional. Heck, I’ve seen this work in most of my startups so far (and it’s really worked out well)!

Starting here is a simple framework for moving the relationship ball down the court (and making sure that the relationship stays intact so that you can improve and work on it!).

Get your team to commit to these things and now you’ll have a shared starting point.


Self-reflection? Introspection? Ugh…!

It’s always easier to focus on “fixing” other people. But, we know that’s only half of the real equation. Spending explicit time working on ourselves is not easy nor is it simple (and it’s harder to do and diagnose).

But we should make an attempt anyway, especially since we’ve just spent a lot of time working focusing on all those “other” people in our lives who need a ton of help, right? Right. Personal evaluation is critical so that resolutions can be authentic, clear, and real.

But even more so, it’s important because we simply don’t want to be victims of repeat offense, namely, we don’t want to make the same mistakes that we seem to make time and time again. If you’re anything like me then you know this far too intimately: We can’t seem to learn from our mistakes as often as we’d like!

Here are some questions that you can ask yourself at any level within the organization, from SME to senior leader:

  1. Are there people in your organization you have a difficult time trusting?
  2. Is it your issue or theirs?
  3. What can you do about your part?
  4. What do you need to address with them about their part?
  5. Who do you sense has a difficult time trusting you? Why?
  6. What can you do about it?

Here’s another principle and fact that’s tough to swallow: Trusting is risky but refusing to trust is even riskier. Trust enables an organization to move fast, stay nimble, agile, and effective.

But, if you’d rather have an organization that is anything but one that has those characteristics then you can go ahead and continue to keep everyone in your organization at arms-length and suspect.

The greatest organizations, especially in the beginning, were built on grit, hard work, and deep-seeded relationships fundamentally built on trust. That’s how startups are born and the character of each team member is the “oil” in the relationship that drives it forward to success.

Reggie McNeal once said:

Teams use trust as currency. If it is in short supply, then the team is poor. If trust abounds, the members of the team have purchase power with each other to access each other’s gifts, talents, energy, creativity, and love. The development of trust, then, becomes a significant leadership strategy.

Trust creates the “load limits” on the relational bridges among team members, staff, and pretty much any relationship. If you have a hard time accessing your team’s gifts, talents, energy, creativity, and love… you probably have a trust issue.

And so we end (and begin) with the leader. I have to begin with me, especially if you’re the startup founder or co-founder.


Time to get your junk together.

The reality is that leadership is stewardship and you, as the leader, are always accountable to it (this is one of my organization’s values!). Trust and suspicion are both telegraphed from the leader throughout an entire department or organization. A culture of trust begins with the leader.

Trust is a choice and when leaders fill the gaps with anything else other than trust they fill the organizational culture with something that ultimately erodes the organizational culture, regardless of style, method, or any top-level strategy. This is where cultural debt begins to build.

And when you can’t choose to trust you must choose to confront. Concealed suspicion poisons the entire relationship, team, and organization. It’s insidious and it can spiral completely out of control. You know this, you’ve experienced it! Mahatma Gandhi has said it well:

The moment there is suspicion about a person’s motives, everything he does becomes tainted.

And sometimes it’s really hard to recover. Sometimes it’s impossible. You know this because there are people in your life where you feel as if you’ll never be able to trust them, ever.

But in the professional context, in business, you can’t just easily quit on someone or just fire them. You have to confront them in a healthy, respectable, and meaningful way.

It is important and it is possible. In fact, the consequences of confrontation are far less severe than the consequences of concealment. The former is tangible, immediate, and impact fewer people. The latter is intangible, long-term, and impacts everyone.

Naturally, to develop a culture of organizational trust the leaders must be trustworthy (and choose to be daily).

Every single day we, as leaders, must make this commitment. It’s not a one-time thing. It’s continual and it should be part of the very heartbeat of our day and, as a result, the very heartbeat of the organization:

To maintain the relationship integrity necessary to operate as a team, we must choose to trust and be trustworthy.

Building a culture of organizational trust is hard, but worth it. Recovery is always possible but it will not always be easy. Again, it’s worth it.

We all have a role and a part to play. We all have control over our choices and how we may respond to the gaps that we see and the expectations that we have. But if we are all truly committed to building a healthy organizational culture we must choose to trust and commit to work on it consistently.


This post was originally written here on my personal blog but I’ve edited the content and updated it. It’s also worth noting that all of this was deeply inspired by the work of Andy Stanley and his staff via North Point Ministries. I worked there for a time and they are directly responsible for crafting my perspectives around leadership and organizational health. I am deeply grateful for the years that I spent there and would not be who I am without those experiences.

Organizational Values Should Evolve & Change as the Organization Scales & Grows

Different colors for different needs.

Within the first few days of putting together a startup I set out to codify the value statements of the organization. This is because I knew that our company culture, both functionally and philosophically, starts on Day #1 and that the elements of that company culture would begin to cement themselves whether I liked it or not.

So, within the first few days of starting (after the insane 72-hour blitz of starting) I sat down and wrote out what I believed should be our value statements. I landed on a few top-level ideas and then began to flesh them out, including some of these that didn’t quite get to the final drafting table:


The point of this exercise was to try to align both what I wanted the company to be and what was really happening — as I had shared in this blog post, there a really big problem in many companies where what is preached is not actually practice:

This is why I think employees and staff become disenchanted with an organization when they quickly realize that there is a huge (and widening) chasm between the written value statements of an organization and the ones that are actually practiced.

I didn’t want to be that type of organization. Why? Because no one wants to work with that type of organization and if you can’t get people to work with you then you don’t really have a company, do you?

Nope, you don’t.


Looking for the elusive (yet similar) value statement(s)…

Value Statements are hard to write because, well, they are just hard to write, for a number of different reasons. Perhaps the #1 reason is simply this: We’ve heard too many value statements that are all fluff and with zero bite and it is just difficult for us to mentally distance ourselves from those “other” companies and the “unique” company that you and I are now building — we want to be different but the values that those companies have and the ones that you want to have are so similar…

This mental exercise is taxing but without good reason — you can have a much more relaxed approach to it all! I think, to start, I hold these two principles in place when I first start writing out my value statements:

  1. Real values are ones that are practiced.
  2. Values can (and should) change.

On the first point I’ve already spoken extensively about that here so I won’t go into that much more, but on the second point it’s worth a much broader look and explanation.

I believe that value statements should be fluid, just as life is fluid and ever-changing. And this is actually in line with point #1 as well — I believe that you can and should write down your values but only write down the ones that you are actually practicing which gives us a very nice angle of approach for #2. And you change what you practice, right?

You see, just as you evolve and grow and change as a person (i.e. your actions change and grow) I believe your company, the organization, the “organism” as a whole, should also grow, evolve, and change as things change. Consequently, as the actions of the organization change this gives you permission to have your values change too (since they should align with your pragmatic and tangible actions).

A healthy and long-standing company will fundamentally change over time and this isn’t just for continued success in one direction; at times it can be for their very survival.

We just saw this with Zenefits who have fundamentally shifted their company with their leadership and direction. David Sacks, the new CEO, even announced a new set of values with this change:

Effective immediately, this company’s values are:
#1 Operate with integrity.
#2 Put the customer first.
#3 Make this a great place to work for employees.

The change isn’t a bad thing or a good thing — it is just a thing that needs to be done to re-align, re-assess, and re-structure for survival and success. As the company changes the values can change too.

And, for the sake of Zenefits and for the many other companies that are fighting for their lives, I hope they can do what is necessary to change even the most fundamental of things to make it through this next trying season.


Your values won’t save you.

Changing your mind is a really healthy thing to do. Unfortunately, we become much more “rigid” (and oftentimes brittle) when we get older as things that were once just mere ideas become crystalized and cemented into who we are as people.

Part of this, I believe, is based out of fear — the world is a big, scary place and as a child we are not fully aware of everything that is ready to kill us (or at least put us in our “place”). As adults, we become much more aware of how little we know and the few things that we do know can become sacred, like a life jacket or life boat.

In fact, sometimes the things that we believe become who we are — you’ve met the type, haven’t you? These people (even close friends perhaps) are so much about this one “idea” that they become known for that idea or perspective or worldview. It’s their “party-line” and for some it can become really sweet and endearing but oftentimes it’s just annoying (and they don’t get invited to parties much).

But there’s something about people who are both confident in who they are and yet are humble to admit when they are wrong or mistaken. These people have that “thing” about them that makes them trusted resources, both in what they have to share but also in how they receive new information with open arms, ears, and mind.

These people are able to change their minds about things, often to their own benefit and those that they work with. I particularly like Jeff Bezo’s approach to this when he talks about changing your mind:

During one of his answers, he shared an enlightened observation about people who are “right a lot”.

He said people who were right a lot of the time were people who often changed their minds. He doesn’t think consistency of thought is a particularly positive trait. It’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicted your idea today.

He’s observed that the smartest people are constantly revising their understanding, reconsidering a problem they thought they’d already solved. They’re open to new points of view, new information, new ideas, contradictions, and challenges to their own way of thinking.

This doesn’t mean you shouldn’t have a well formed point of view, but it means you should consider your point of view as temporary.

What trait signified someone who was wrong a lot of the time? Someone obsessed with details that only support one point of view. If someone can’t climb out of the details, and see the bigger picture from multiple angles, they’re often wrong most of the time.

I love that a lot and I think it aligns well with the idea of a more fluid approach to value statements. It’s this simple yet profound idea of having strong ideas loosely held that I characterize those that are able to not just survive but thrive in an ever-changing world and economy.

So, when I first started my new company I wrote down the values that I believed to be true that day, based on empirical evidence, and believed them to be strong values that could be shared with enthusiasm and strength.

But, as we change as a company and organization, I’m fine with them changing as well — and if what I believe about culture is true (that “culture” is, among many things, the aggregate of the people that work with you) then it should naturally bend and shift as we grow and scale.

With that in mind, below is what I penned for TOMO a few days after I got started and our current 4 value statements, knowing fully that they will (and should) change as my company changes.

It’s a scary proposition and idea, but that’s okay — if we’re going to try to achieve all that we want to achieve then we’re going to have to be the type of company that isn’t myopic or close-minded in who we are as an organization (and it’s my responsibility to set that tone and pace).


A north star… one of many.

Our values are the very heartbeat of who we are and why we do what we do. Although writing these down feels somewhat insufficient it’s a great place to level-set the entire organization.

Most organizations have “Value Statements” because they believe that they should have them and then give them lip-service and do not actually practice them at all. A good litmus test for whether a company lives out their values is to ask any of their employees what they are — most will not be able to name them, to say nothing of actually being able to describe their day-to-day utility.

At TOMO, we built this company on the very values that you see below. In fact, this was the very first document that was ever created, before any of the first lines of code were written and way before any official business docs were signed. We believed that if we were going to build a successful company that it require rock-solid values and a commitment to actually live those out in our daily lives.

Consequently, we hope that you breath in deeply our values and that they ultimately become your own; and, that you use them as guideposts for all of your interactions with others here at TOMO (and beyond)! You will find them approachable, useful, and infinitely scalable.

1. Health

We believe that we do our best work when we are in the best shape, physically, emotionally, and spiritually. We will take the necessary time to rest, to recover, and to allow wholeness in our lives. We cannot fulfill our mission if we do not first have the most organizationally healthy company on the planet. We must be the model of what we hope and believe our customers can achieve.

2. Leadership

We are a leadership organization that purposefully attracts, hires, and invests in the leaders of our future. We believe that leadership is stewardship, it is temporary, and we are accountable to see it blossom and grow in ourselves, in our team, and in the organization. We fundamentally believe that leaders exist to serve others (not the other way around) and we will mentor and coach our staff to be their very best selves.

3. Relentlessly Resourceful

We are building a solution that everyone knows they need but that no one has ever dared to build in a world that is resistant to change. To survive we must be willing to experiment quickly and intentionally, be fearless with our execution, and be willing to create new and misunderstood solutions in an environment of ambiguity. We will accomplish this as a team and we will thrive.

4. Trust Over Suspicion

We’re all human and we know that there will be times where there will be gaps between what we expect people to do and what they actually do. But there’s a huge opportunity here for all of us as we get to choose what goes in those gaps and, at TOMO, we intentionally choose to believe the best instead of believing the worst. We need this because trust is the fuel that will propel us forward, together, and we commit to actively engage with each other when we feel like that trust is being challenged. This isn’t easy but it’s worth it.

Please read my larger post about this topic here:

Organizational Trust

At TOMO we are fundamentally changing the way people transact and authenticate their identities online and want to help build a truly “paperless” world. We’re attacking this problem first in the HR segment but this is just the tip of the proverbial iceberg.

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2016 Headshots

Managed to snag a few headshots for this new year and for a new startup I’m putting together, TOMO, with my cofounder Billy.

There are two significant differences between these new ones and a few that I had done 2 years ago: The first is the depth of the wrinkles on my face (especially under the eyes) and secondly the obvious increase of grey hair.

Yikes. I’m getting old.

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