3 Ways to Build Trust at Early Stage Startups

Alli at Yesware
Ali Jawin, Marketing Manager at Yesware.com, a Boston-based Sales Acceleration tool for Gmail and Outlook. Yesware has raised approx $33M across 5 rounds (source: Crunchbase)


Engineers: better at speaking Klingon than speaking to people
Salespeople: bros pounding beers and extra cruelty McDonald's fries
Marketing: destroyers of truth and purveyors of evil
Office admin: the end of fun

No matter your role in an early stage startup, we all know these stereotypes. It is also fair to say that no matter your role in an early stage startup, there is a grain of truth in all of the above claims. So, you find yourself at an early stage startup (less than 80 employees, pre series C) overwhelmed by what I call #allofthethings, and you find yourself in tension with colleagues - especially colleagues in other departments.

Tension between departments and colleagues in and of itself isn’t a problem - even in the idealized world of the TV show The West Wing people disagreed and had competing motives and priorities. A lack of trust, however, derails a company faster than any outside factor.

Once you don’t trust that a colleague has your back, knows what she is doing, isn’t a spy for a competitor or foreign government/agency, etc., you are no longer focused on your job; you are worried about where you stand in relation to others, what other people are really working on, what don’t you know that your colleagues knows… Before you know it the company suffers from the distraction and people quietly polish their resumes and take calls from recruiters.

There is no easy way to build or maintain trust, especially in an early stage startup where the highs are like conquering the world and the lows are uniquely depressing. That being said, there are three things you can do to build trust.

Principle of Charity

In academic philosophy, the “principle of charity requires interpreting a speaker's statements to be rational and, in the case of any argument, considering it's best, strongest possible interpretation.” When applied to tech, I take the principle of charity to entail: assuming your colleague isn’t stupid, lazy, hell bent on destroying the company, etc.


Sounds obvious, but haven’t we all been in a meeting where we thought that someone’s idea was the WORST thing the company could do and would singlehandedly doom the company? For example, Bob thinks it’s a great idea to give away your product for free, but you know that this is an awful idea. When something like this happens you can either 1.) think that Bob is an idiot who has no idea what he is talking about, or 2.) remember that Bob wouldn’t be at your company if he was an idiot and he is good at what he does, so let me ask Bob his reasoning behind his idea in case I am missing something.

By treating Bob with the principle of charity you have the chance to find out where Bob is coming from. Maybe upon further discussion you realize Bob’s idea is great; wonderful, you didn’t prevent a brilliant idea from coming to pass because of a misunderstanding. Maybe Bob’s idea has merit, but it doesn’t take important factors into account; fine, you can compromise, tweak and discuss until everyone feels their concerns are addressed. Maybe Bob’s idea is in fact terrible; so what, the idea is no longer in play, but by treating him and his idea with respect you haven’t created resentment or lingering hostility.

The downside of the Principle of Charity is that it is hard to remember when you are stressed, which is most of the time at an early stage startup. Thankfully there are two things you can do that make applying the principle of charity a habit.

1. Never undermine colleagues
Marriage counselors stress that you should never undermine your partner to others and the same goes for department leaders at any company, but it is especially critical at early stage startups.

Imagine that the VP of Sales and the VP of Engineering can’t agree on whether a product is ready to be shipped. The VP of Sales argues that if the product doesn’t ship now, existing customers and prospects will flee to competitors; the VP of Engineering insists that if the product ships now, the product will be so shoddy that customers and prospects flee to competitors. The VP of Sales counters that without the product sales can’t make its numbers, causing investors to lose faith in the company and putting future funding rounds at risk. The VP of Engineering counters that investors will lose faith in a faulty product, and not hitting sales quota for a quarter won’t derail the company.

Both VPs have valid points and there is no way of knowing with any degree of certainty which path is better. But, if both VPs complain to their departments, distrust between the departments is inevitable. If the VP of Sales complains that engineering cares more about building the perfect product than about the company’s success, the sales team takes that not only as truth but also as license to complain about engineering themselves; if the VP of Engineering complains that sales complains more about their commission then the company’s success, you see how this goes.

By no means should people pretend that there is never disagreement – people will assume you are either lying or out of the loop. A better way of conveying disagreement with respect is to say that a decision has been made, yes its not the one that we wanted, but here is why the decision is made and this is how we are going to do everything humanly possible to support it. For example, a VP of Marketing tells her team that engineering resources aren’t going to a marketing priority, and that she argued for it, but the decision was made so this is the new plan and this is how it is going to be great.

2. Remember the Dark Side of Transparency
The case for transparency in startups has been made, and if you are not yet convinced read this article by CEO of Yesware Matthew Bellows and you will be.

A rarely discussed drawback of transparency is that if negative things have been said about anyone ever, people will find out. Case in point: a recruitment room in Slack or HipChat. Current employees look at the room to see what people thought of a new hire during the interview process, and new employees will check that room to see what their new colleagues thought of them during the process. If negative things were said, a new employee starts off without the respect of colleagues and the employee is hardly setup for success.

Transparency requires a commitment to basic human decency – writing in Slack that you don’t want to make someone an offer because she doesn’t have experience in X and you don’t have the bandwidth to teach her is a nicer way of saying she is an idiot for not knowing X and you have no use for her because she is too stupid to pick X up. That actually happened to a friend when she scrolled through Slack on the first day of a job at an early stage startup.

Transparency isn’t something that only applies to public communications. New people get invited to private Slack rooms and people get CC’ed and added to emails. If a startup is committed to transparency it has to be equally committed to decency.

Long story short, the best way to build trust at an early stage startup is to assume your colleagues aren’t stupid and/or evil and treat them as such at all times.