I hate firing people. It’s the worst part of my job. Even after all these years I still spend days or even weeks agonizing over a decision to let someone go. I feel absurd complaining about this, given that of course it’s a hundred times worse for the person being fired than it is for me. Still, I hate firing people.

My first firing at Top Hat was our VP Sales. He was employee number two, he joined right after we raised our angel round. In retrospect it was doomed from the start, and it was entirely my fault. I had no idea what I was doing when it came to building a sales organization and brought him into a role that didn’t make sense (read about the lessons learned in building a sales team). It took me 6 months before I finally pulled the trigger. In the end, it was undoubtedly the right decision and set the company back on track. But at the time it was an extremely tough call. It was admitting failure – to myself and to our investors – that this first major hire was a mistake. I felt  ashamed about it for months and kept convincing and re-convincing myself that we could still make it work.

As a general rule once you’ve lost faith in an employee, things rarely get better. You can sometimes fix a skill-level problem by giving someone time to grow, but you can never fix a personality problem. If you’ve identified that someone isn’t a fit you need to move on it quickly and decisively. The longer you wait the worse it will be for both parties.

Firing is an essential part of running a successful company.

In a narrow way, it’s actually more important than hiring. You could, in theory, use a shit-against-the-wall style hiring strategy and as long as you filter out the bad apples quickly enough you’ll be able to build up a functional team over time. Of course that’s probably not the best approach.

The reality is that even the most effective interviewers are rarely more than 70% or 80% accurate. The average interviewer is quite a bit worse than that and isn’t much better than chance – often even worse, because the naive approach just selects people who are great in interviews, which disproportionately selects for bullshitters. However, even if you’re some kind of super-human talent screening machine with a 95% success rate, that 5% will accumulate and degrade the culture until you’re surrounded by bozos.

The Best Firing Process is a Better Hiring Process

Of course the best “firing process” is not to have to fire people, which can only be done through effective hiring. That being said, not having an effective firing process is like not having an immune system – the first cold will eventually kill you.

It’s fairly common knowledge these days that A players only like to work with other A players. A slightly more subtle observation is that someone’s status as an A player isn’t fixed. Bringing a weak player onto a team has a tendency to poison the culture and downgrade the rest of the team (especially if that weak player has a shitty attitude.) This bad apple syndrome has been observed to happen fairly reliably in studies on organizational dynamics.

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The Bad Apple Syndrome

We’ve experience this at Top Hat a couple of times. One of the most instructive was with our inside sales team. Early on when we were in a pinch to fill the team we lowered our standards and brought on a few people that we should have passed on. The results were disastrous. The quality of the team degraded and eventually hurt not only the inside team but also other parts of the company that came into contact with it. It took nearly a year of solid effort to rebuild the team. For a time it seemed hopeless. No matter what changes we put in place, no matter how much talent we threw at the team, the cancer of negativity and poor morale just wouldn’t go away. The most profound mistake we made in the process of trying to fix the team was to keep those who were performing well but had a negative attitude.

There was a pattern we observed a few times: we’d put a new person into the team, their performance would be great and they’d be super enthusiastic. Then like clockwork after a week or two their numbers would slowly drop, and they’d become engrossed in the culture of negativity and gossip. It was only after the cleared out the ringleaders who were perpetuating the negativity (who happened to have decent performance numbers!) and put in strong positive management that things finally began to change. The most amazing thing is that many of the people who were B or even C players when the team was dominated by negativity shot up to solid A player status. The overall output of the team per person went up by nearly 300%. In addition it seems as though life was trying to setup a lab experiment for us to prove just how much things had improved – we had a person who had left the company a few months prior re-join the team. His feedback was that he was blow away, he couldn’t believe it was the same team.

Lessons Learned

The first lesson we learned was that no matter how strapped for manpower you are, no matter how much it seems like the world will end if you don’t fill a position, compromising on the quality of talent will surely be more damaging. Second, we learned that in fixing a damaged team the key is to identify the cultural sources of the underlying problem and focus on those. Finally, we learned to use a divide and conquer approach – we would pull all the top talent into a separate team while rehabilitating the broken remaining team separately – it really helped prevent the “negativity cancer” from spreading while we were fixing things. These are simple things in retrospect, but it took a while to pull it off.

One of the most revealing questions I tend to ask when interviewing potential managers is whether they’ve ever had to make the decision to fire someone. The answer and subsequent discussion usually tells you two things: first, it tells you if the person has ever had to deal with the most difficult problems in management, second it tells you if they know how to handle those problems through the process they followed. Assuming the person has ever had to hire and manage a team of a decent size for any length of time, it’s almost certain they’ve made hiring mistakes, and their answer tells you that they know how to detect and correct these mistakes. If the person simply walked into a mature team, or has had HR handle all the hiring/firing decisions for them, then they’ve been living on easy street.

The process of firing someone is always somewhat unique to each situation. That being said there are some basic principles that you should always follow:

  1. Give people plenty of notice and regular feedback. Give people several chances to improve. The actual firing should never be a surprise – if it is then you almost certainly did something wrong in setting expectations. Depending on the role the whole process should take 1-2 months (longer for senior roles.)
  2. Try to be generous with severance and leave the person in a good spot to find their next employment. I know it’s not always possible in a startup, but do what you can. It’s the decent thing to do.
  3. Take time to reassure the rest of the team and explain (with discretion) the process that was followed and why the decision was made. Letting someone go is always a huge morale hit (even if the person wasn’t well liked, it still scares people.) You need to make people understand that their job is not in danger.

Firing someone is always a brutal experience. Anyone who says otherwise is either lying or is a psychopath. That being said, it’s unfortunately a necessary evil and understanding when and why it needs to be done is essential to the success of any business.

Michael Silagadze

Mike is the founder and CEO of Top Hat Monocle. He is an engineer from the University of Waterloo.

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GROWtalks

Debbie Landa, Clare Ryan and the Dealmaker Media team are part of the reason that I love GROWConf and GROWtalks. They put on amazing events by putting entrepreneurs first, foremost, and front and centre. They are bringing GROWtalks to Toronto (Feb 21) and Montreal (Feb 19). And we have a discount code at the end of the post.

“A hands-on playbook for creating startup success”

I like learning by example. It’s a mixture of seeing what worked for someone else, and then trying the appropriate tactics customized for my situation. The challenge is trying to do with more efficiently than 9 or 10 coffee meetings. GROWtalks brings together the best entrepreneurs, who are killing it, and has them present what is working for them. THis is what GROWtalks is, an event for entrepreneurs with entrepreneurs sharing their strategy, tactics, metrics and successes, even the failures. (Full disclosure: I am MCing the GROWtalks event, however, I am not being compensated for this, but I do get the opportunity to participate and learn).

Check out photos from the 2012 GROWtalks event in Vancouver:

It’s rare we get this many awesome startup founders all talking about the hard part of their business. I know that all of these folks will be around throughout the day, they’ll be hanging out, answering questions. It’s going to be a fantastic day. Check out the line up:

I might be biased. My employer is an investor in some of the presenters. My cofounder is one of the presenters. But I’m honestly stoked about the speakers. I’m really looking forward to hearing Beltzner, Rutter, Fitton and Morrill. The mix of product, early customer acquisition and understanding lifetime value are converations I have with almost every founder. I’m very curious to hear the opinons, experiences and thoughts of this group.

Part of my MCing was to request StartupNorth logo tattoos for all the speakers (we’ll see if that happens), and a discount code. Register before Februrary 1, 2013 and get 10% off (use promotional code: startupnorth). It reduces the ticket price from $195 to $175.50.

GROWtalks Toronto

February 21, 2013, 10am-4pm

Size: 200-300 people
Speakers: 9 Industry leaders
Time: 10am-4pm
Website: www.growtalks.com
Toronto: http://www.growtalks.com/events/toronto/

GROWtalks is a one day conference focused on how to create simple, actionable metrics, and use them to make better product and marketing decisions for startup success. Industry experts will share actionable advice to startup teams on how to improve design, product and customer development, acquisition, retention, and more.

Topics Covered:

  • Customer Development
  • UX/UI Design
  • Growth Hacking
  • Customer Retention
  • Fundraising
  • Customer Engagement
  • Product Development

David Crow

David Crow focused on product design, customer development and go-to-market implementation on $0. He is available as a consultant. He is a mentor at UW VeloCity, Jolt and FounderFuel. Follow him on Twitter @davidcrow or at DavidCrow.ca

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I keep having a similar conversation with early stage entrepreneurs about fundraising and valuation. “Do you think a $1.5MM valuation is good?” “How much should I be raising?’ Well, it depends.

I’m finding more and more, the conversation about valuation is one that resembles not being able to see the forest because of the trees. Early stage entrepreneurs tend to fixate on valuation and assume product is the biggest risk at the seed stage thus defining product launch metrics as key metrics. Often, valuation and risk mitigation are tied together. And the milestones or traction metrics required to mitigate risk can help establish valuation. 

Valuation

Fortunately, valuation is a topic that others have covered. Nivi and Naval, on VentureHacks, have provided incredible insight into early stage fundraising over the past 5 or 6 years. The advice is often summarized, “as much as possible is especially wise for founders who aren’t experienced at developing and executing operating plans”. The translation means that founders see rounds of seed stage companies raising $4.2MM at what must be a huge valuation.

 ”‘As much as possible while keeping your dilution under 20%, preferably under 15%, and, even better, under 10%.’ ” – Nivi

You can make some basic assumptions about the valuation. Most seed stage companies should be looking keep dilution in the 15-20% range. The specifics will be determined in fundraising but you can start to do some back of the napkin estimates:

You start to see a range for how much a company will raise at what valuation. The numbers aren’t set in stone but they provide a framework for estimating the amount valuation. As Nivi points out the difference between a seed round and “a Series A which might have 30%-55% dilution. (20%-40% of the dilution goes to investors and 10%-15% goes to the option pool)”. The more you raise early, the more dilution you can expect. The goal becomes managing the different risks associated with startup. You also see why raising debt early, which allows companies and entrepreneurs to delay valuation until certain accretive milestones, is attractive.

“The worst thing a seed-stage company can do is raise too little money and only reach part way to a milestone.” – Chris Dixon

So given the back of the napkin dilution terms, what are the milestones that you will need to hit in order to raise the next round.

Raising the next round

So you’ve raised a round, how much should you raise at the next round?

I like the rule of thumb that Chris Dixon uses. “I would say a successful Series A is one where good VCs invest at a pre-money that is at least twice the post-money of the seed round.” The expectation is that companies are roughly going to double their valuation at each raise. This isn’t to say that a 2x increase in value is your target, it’s the minimum, the floor. The art of raising a round it to raise enough money to get to a significant milestone, and not too much money taking too much dilution too soon. So how do you define the milestones. The milestones

“partly determined by market conditions and partly by the nature of your startup. Knowing market conditions means knowing which VCs are currently aggressively investing, at what valuations, in what sectors, and how various milestones are being perceived.” – Chris Dixon

So part of the market conditions, i.e., raising money in Canada is different than raising money than in Silicon Valley, New York , Tel Aviv. You are measured against your peers, and this might be defined by geography of the company or the VC. Being connected with other companies, advisors and investors can help provide insight in to the fundraising environment. The second part is determined by the nature of your startup, but generally expressed as measures of traction. We’ve talked a lot about getting traction and what traction looks like to a VC.

“The biggest mistake founders make is thinking that building a product by itself will be perceived as an accretive milestone. Building a product is only accretive in cases where there is significant technical risk – e.g. you are building a new search engine or semiconductor.” Chris Dixon

Entrepreneurs tend to focus on the product early. This is usually because the product is something that entrepreneurs can directly affect. But the product risk, is may not be the  biggest risk that entrepreneurs need to mitigate early. The trick is figuring out which risk you need to eliminate to satisfy potential investors. And you can try to figure this out yourself, but I like to see entrepreneurs engage investors and other founders to get their opinion. The discussion usually is a combination of what other startups are seeing in the market place as milestones from investors (yay, market place data). Then you can work backwards the necessary resources and burn rate to reach those milestones.

Thoughts?

Additional Reading

David Crow

David Crow focused on product design, customer development and go-to-market implementation on $0. He is available as a consultant. He is a mentor at UW VeloCity, Jolt and FounderFuel. Follow him on Twitter @davidcrow or at DavidCrow.ca

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