Startup Lessons Learned: Can You Be a “Friendly” Boss?

startup lessons learnedI was recently spending time with a good friend of mine, he’s a hot shot professor of design in Switzerland.  Tom also has his own design firm and had just brought on a couple interns. He was talking to me about an issue he had with them.
Tom had invited them out for a night of fun – drinking & dancing to a well-known DJ going late into the night. But there was an initial agreement. If he allowed them to join him, that the next day they needed to deliver some initial design comps for a new product line. And…they kind of dropped the ball. Our buddy is a very nice guy, and was feeling frustrated about the line between ‘friends/friendly’ and being an effective manager.
It brought up a dilemma many managers face – can you be friends with your employees? My buddy Kevin O’Leary (Shark Tank, Mattel) says “your employees are not your friends” and I get it. It can remove objectivity and jeopardize your business decisions. But, if you already crossed that line,  how do you manage this issue to success?
It’s actually very simple in theory, but 100% necessary to execute, especially if you are a ‘friendly’ type of manager:
  • Establish clear goals from the beginning – don’t beat around the bush
  • Lead by example – have fun but get your business shit done
  • Address & resolve any issues immediately – nip any issues, even if they seem minor, in the bud. Once you let something slide, you are on your way to failure. Your employees deserve to know your thoughts so they have a chance to improve.
  • Establish boundaries and if they re not respected you have the wrong people, friends or not
  • And, if it isn’t working, take the hit – fire if necessary. BUT take a close look at yourself and change your management style. Because it’s all about Business First.
Hey, I’ve lost friends because I had to fire them, and wish I would have never hired them in the first place. So don’t misplace friendship for objective business decisions and for new folks you hire, it’s OK to be ‘friendly’, but watch that line!

Startup Lesson: Business Process Focus – When Your Team Is Under Water

Cartoon about business process for business dashboard startup DasherooAhh, start-up land…finite resources and infinite things to get done! And all of those projects can appear to be critical to your success – or survival – right now. And if you don’t have a clear business process, you and your team can feel, well, under water.

At our business dashboard startup Dasheroo, we’re so excited to launch new features, integrate with more applications, get more traffic in the door and improve our in-app experience, that it can be dizzying at times.

And recently, I started to feel the springs almost starting to pop. You’ve probably been there, too. Progess? Sure, but not enough projects getting pulled over the finish line. Too many projects stuck in that ‘WIP’ category for too long.

And when that starts to happen, it’s time to reboot! And that means regrouping with the team, having an open discussion, focusing on the real priorities (maybe re-prioritizing), a real business process and executing.

We had a great meeting recently, where we revisited each major deliverable for Q4 across marketing, product, sales and engineering. It resulted in us taking a few things off of our plate, at least for now. Just agreeing that “we’re not gonna do that”  this quarter. Or, “we thought that feature was really important a few months ago, but now that we’ve learned more it really isn’t mission critical'” It’s sobering, necessary and productive.

So what are some of the actions we took?

  • We delayed one big engineering project to Q1, and re-scoped another one that dramatically reduced (almost eliminated) additional engineering time. That meant we can focus on and complete a couple immediate revenue-generating projects – Insight alerts, branded dashboard exports and an agency & partner console that were all stuck in that ‘we’re almost there’ category.
  • We took a hard look at which social media and content outlets were providing us the best (and worst) results, and adjusted our publishing schedule to optimize the time spent on writing and socializing articles so we could spend more time developing a pricing test and a new onboarding experience.
  • We decided to take a couple app integrations off the Q4 table and focus on two key integrations that are more deep, more valuable and focused on driving user acquisition in a key market.

Although these discussions usually come a little too late, it’s the nature of the beast. I’ll try to get a better read on the ol’ ‘under water’ crystal ball, but the bottom line is addressing these issues immediately, getting everyone on the same page, and executing!

How do you identify and resolve business prioritization in your company? Let me know!

Startup Lessons Learned: Harmony Sucks!

let's settle this like adultsOK, sure – harmony can definitely be a great thing. But I thought ‘harmony sucks’ might get your attention! And I do believe that harmony sometimes really can suck: it can suck your ability to confront potentially thorny, uncomfortable issues with your team, partners and investors. Which in turn sucks the productivity out of your business.

The Heat is On!

Several years ago, this really hit home for me. The software company I ran a large division of had just acquired another software company of 100 or so people in Iowa and I took over running it. One of the first meetings we had when I landed in Cedar Rapids was attending their exec ops meeting. I really didn’t know what to expect, so let them know I mainly wanted to watch and listen to a typical meeting, and begin to participate after a meeting or two.

I’d never been in a meeting where there was so much heated debate! It even made me a little uncomfortable. People were fighting for their own P&Ls. Making the case for (always) limited resources to be directed to their cause. And they immediately drew me in for my perspective, which I provided by explaining how their goals flowed into the new parent company. And we had some great back and forth on my views too, which we all benefited from.

At the end of this 2-hour meeting, even though everyone didn’t get their own way, the team came away with a clear understanding and respect of ‘why’ the decisions were made, and everyone bought off and got behind getting those actions done. Later, I asked the controller JoAnn if that was a common exec ops meeting, and she assured me that ‘yes’, they approach each of those meetings very seriously, but with mutual respect and always a clear understanding of the tactics and strategy that maximizes the vale of the business. And sometimes it gets heated, and sometimes it doesn’t.

I’ve tried to apply that way of thinking and acting since then.

The Board is Not Bored

We have the best investors I’ve ever been involved with, and the sharpest board as well – board members and advisors alike. At a recent board meeting, we had our most ‘spirited’ meeting yet. Yeah, it even got a little contentious around our discussions on product and my approach to target markets. And you know what? It was our most productive board meeting yet! We all have passion, and that passion came through in very candid discussions around maximizing the value of Dasheroo. We came away with a clear understanding of each other’s views and an action plan we all could get behind and execute on. And most importantly, we all showed the respect we have for each other.

It reminded me that I need to apply ‘non harmony’ not to just our exec ops meetings more often, but in our daily work routine as well; sometimes everyone would rather just ‘get along’ and not surface an issue that may lead to conflict rather than dive into and resolve the thorny issues that are bound to arise in any company.

Question the Boss, They Don’t Know it All

I used to consult for a public company that was stuck in the passive harmony state. I quickly decided to leave, as no one wanted to stand up for what they believed was the in the best interests of their customers. They’d just all do what ‘the boss’ said, and go about their day, never achieving things that they felt were important. It was like living a Dilbert cartoon! Yup, it can infect big ‘ol companies too, probably  more often than scrappy ‘lil ones like Dasheroo.

Startup Lesson Learned

It’s easy to go with the flow, and maybe not confront an issue that is really important to you because it might ruffle feathers. You may have to go the extra mile to defend your position, it may not be popular, and you could even lose your argument. Whatever. Get over it. If it’s in the best interest of adding value to your customers and your business, stand up for what you think is important. But also, know where to draw the line, and pick your fights wisely. Too much conflict can also destroy your team’s passion and productivity. And always: show respect.

John@Dasheroo
Co-founder