Mistakes In Hiring

Below is a collection of mistakes I’ve made as an early, inexperienced manager and employee. I also enumerate mistakes I’ve seen made. The hope is that it adds to the wealth of literature and opinions in this space.

Mistakes I’ve Made

Needs And Goals

I hired without being able to clearly articulate a very specific set of needs that aligned with company goals. Clearly my team needed help: we were overworked, there was plenty to do, and we had a looming deadline. In a fast moving environment, solving problems quickly and showing results is key. Hiring people is one way to show that things are getting done. Unfortunately, when you’re throwing darts at the wall, you either get lucky (ie. finding the perfect people for your team, which happened), or you miss completely (ie. adding the wrong people, which happened). If I had spent time understanding where we were struggling (assessing our needs), and what we were trying to build (understanding our goals), this would have resulted in an order of magnitude improvement in identifying the right candidate (needs aligned with goal). Thinking allows you to build a quantifiable framework that can be tested against a variety of hypotheses. Without metrics, you can’t systematically improve.

Alignment In Expectations

I hired without being aware of the responsibilities and level of ownership required to meet our business and team goals. I had the unique capability to bring in people and get them excited, but ownership/responsibility (asymmetry of expectations — the person getting hired thinks one thing, the person hiring doesn’t have a clear idea of the ownership scope and expects them to “do it all”) was thrust on them, creating a needlessly stressful environment. The antidote for this is clarity: understanding what you’re building, and a general idea of framing the problem and design in terms of requirements gets your very far. A concrete specification gives you something to iterate on, whereas pure intuition relies on past memory and is prone to failure.

Bargain Hunting

I’ll never try to hire folks at a bargain — seen it many times, I’ve been the asshole who did it, and I’ve had it done to me. That creates unnecessary stress, resentment, and animosity. Pay people what they’re worth. Maybe pay them a little more. Put skin in the game (in regards to testing your process) — refine your process, and if it works, you’ll be getting really good people so bet on your process and your people. Let them know that you care.

Mistakes I’ve Seen Play Out

Hiring Fast

Hiring too quickly for the sake of hiring. This creates stress on your team if you don’t have a rock solid process, brings down the quality of the team, and can cause a misalignment with your product priorities (hire a person that’s great at X, but you really need Y). Your employees are the base of your company. If you’re hiring someone that isn’t aligned with your organizational goals, you’re creating a weak structure for your company, making you less resilient and more fragile to internal and external shocks.

Expectations

A lack of a feedback loop between you and your direct reports fosters uncertainty in expectations, deliverables, and, as a result, decreases performance. Instead do: continuous feedback, mentoring, clarification in communication, celebrate the wins, optimize away the losses. Cut those that end up not fitting the culuture or living up to expectations, but not before pouring blood, sweat, and tears into them first.

Salary

Startups relish in the art of undercutting folks to a disgraceful degree. A common mistake is to compare salary to past experiences or mental expectation (anchoring the team low) rather than a model based on data or the market. Counterpoint: people end up working regardless of [low-pay] because they want the [brand] and [experience]. Unfortunately, from my experience, there never is an increase, and this creates unnecessary resentment and stress. Eventually when growth stagnates and pay is low, people will leave. Paying your employees well (and continuing to pay them well) is incentive-compatible. If you’d like them to leave, stop investing in them.

Hiring Funnel

Always. Be. Hiring (the process, not the activity). The funnel should always be on. Resumes should be sifted through continuously, put into piles (no, yes, follow up in the future). Always take coffee meetings. Screen people when possible. Make it a part of the culture. Even if there’s a hiring freeze, there are always exceptions to the rule. There’s that person that can 10x your business by being the multiplier to your team. Move mountains for that person. Timing is everything — if you’re always on, you’ll catch the elusive person you’ve been trying to hire. I’ve seen a failure to do this and it ALWAYS blindsides companies: when they most need candidates is when they start doing the things they need to (but by then it’s too late).

Culture

Thinking that culture isn’t a day 1 thing: if you don’t dictate and control it, it will control you. Marginal additional effort expended on culture (behaviors, processes, office space, working conditions, interview process, negotiations, …) yields compounding dividends later. Most startups assume culture is something you do when you’re winning. This is incorrect: winning is a culture. A solid culture is most needed when your organization is failing due to a misalignment. Stories have aligned individuals for a greater purpose for millenia — don’t reinvent the wheel.

There’s an enormous amount of literature on things that work well for companies of all types and sizes. People like Keith Rabois and Elad Gil have spent a ridiculous amount of time thinking deeply on this subject, putting it into practice, and writing/speaking on the topic.

Thanks to Shantanu Joshi, Imaad Rashied, and Radhika Gulati for reading early drafts and helping clarify thoughts.