Troublemakers You Meet in a Start Up

The 7 Troublemakers you meet in a start up

One of the greatest adventures in life is working within a start up. The twists and turns across uncertain and unfolding landscape can make a veritable roller coaster. That uncertainty and potential tend to draw a cast of characters as participants. Some are memorable. Here is my list of 7 troublemakers (not all inclusive by any means but these are favorites) that you meet in a start up.

1. Ms. Strategy

This capable, driven, articulate young lady will meet any requests for tactical execution with a discussion of strategy. In a start up, everyone is close to both the strategy and the supporting tactics. Some people can't help themselves from knowing better about either or both. Plus, talking is a lot easier than doing.

2.Mr. Big, Hollow, Pipeline

He made $300k at Cisco before taking this job. Now he has a huge sales pipeline of brand name companies with massive revenue potential and no disciplined approach to characterizing possibility of closing them. Ask him how a 30% likelihood of close defers from a 70% likelihood of close and he will talk about people and conversations rather than steps and actions. I now assume that Cisco pays all failing salespeople $300k.

3. Goldilocks

The ever changing roles and challenges of a growing start up provide an endless set of opportunities to try new jobs and responsibilities. Most people love being stretched and many discover or develop new skills or interests. Not Goldilocks, however, as this individual tends to be too heavy for light work and too light for heavy work. In any other words, no matter what the challenge or organizational needs at hand -- Goldilocks will fail you.

4.The Big Time Scaler

No sense building any system today that won't scale to size of General Motors. Yes, every start up organization has plans and dreams but sometimes you need to sell one house to get another, larger one rather than live in a mostly empty, expensive one along the way.

5.Mr. Artiste - the programmer

He is creating software (sometimes the company's core product/hope of future success) and he isn't limited by the contents of the requirements document. He isn't limited by it because he isn't reading it. He is creating, damn it, and brings his own vision. Definition: Artiste Plus, staying consistent with his vision keeps him closer to his imaginary specification with its imaginary time line (and yes, he's on schedule).

6. The Holiday Maker/Union Rights Leader/Salary Surveyor

Yes, a long title, but its a big job. First, this person will seek the addition of incremental holidays to the company calendar. What no Veteran's Day? We don't get off the week between Christmas and New Year's? Friday before Easter or the Monday after? Well, you get the idea.

This contributor will also "represent" the feelings of employees to management without consulting many of them first. There's no who in this group, its a group of "everybody". So, if you're a company leader and you ask "who" said that, the probable response is that everybody says that. Unless, the question is "who thinks I'm being a jerk about this?" and the Union Leader has a score to settle with someone.

Finally, this person usually investigates and shares salary data for the purpose of fomenting general dissension within the company. This can be useful between two parties or as another representation to management -- "People are unhappy that Sam makes so much" or "People over at comparable start up make more than us". You might ask how do you know this information but the source will be akin to "that's what I'm hearing". It is also fun to say "Do you think Sam is fairly paid or could you do his job?".

7. The Angry Support Person

I can never figure out what makes them, or keeps them angry, but they can be the Energizer Bunny of anger. Maybe the line of work, or being the starting point of a feedback loop for whatever is going wrong with the product or customers, but in any case, the Angry Support Person can create a special kind of crisis. I had one tell a customer to "F#@$k off" and another talk obscenely with a customer (apparently to the delight of the customer but displeasure of co-workers - so maybe not an Angry Support Person in the technical sense).

Here are some additional Troublemakers........

6 More Troublemakers you meet in a start up

Image via Wikipedia

Start ups attract and often feature some memorable characters. Consistent with my previous post on the subject, here are 6 more troublemaker favorites.

1. The IT Support Guy/ Flannel Bob

He's busy but he is working? Does every computer need to be taken apart?

And how come you can never make a point that he doesn't already know about like "Did you see the next version of this has that? or "I saw they're coming out with ...." Answer is always, "Yeah, I saw that."

And talk about an understated flair for the dramatic, try "The company is going to run out of disk space in an hour" (Hmm, that gives us plenty to time)

OR "I sent a note that the email system is down". (Helpful)

OR "What you are asking for simply can't be done" (It is outside the scope of human endeavor)

OR "You should know how to do that". (And you should know I want to kill you)

OR "For me to know how to do that, I need this $2495 training out of town for a week".

(The training certification will be on his posted resume at Monster before he returns to the office)

The IT support position in a start up is no small job. The person is invested with near magical skills from the perspective of peers and yet, manages to consistently disappoint 90% of he deals with. That isn't easy. Defeat is stolen from the jaws of victory by dispensation to most, but not all, of a task. So the printer is installed but it won't print correctly from your computer. Installed printer, you didn't say to test it....

2. The New Marcom Manager/ Captain MoonRocket

He is much cooler than you. He dresses better. And he has come up with a new campaign to re-position the product and company. You just don't know how a picture of a rock in a bed of sand does that. It makes sense to him. Just not to you. Or anyone else. But boy he is convinced and it is as if he needs to reach across the time/space dimensions to reach you. He can really talk with his hands and his framing gestures are intended to create breakthroughs in your understanding. Where did he get those glasses?

Speaking of rocks, and if he isn't stoned, shouldn't he be? How does he talk like that?

3. Joan of Accounting/ Defender of the Realm

New customers and, worse troublesome accounts receivable, just make more work for her. If good accounts don't make it through her screen, it is just less work. Since the collection of bad debt will inevitably fall to her, she sees her primary job as the prevention of bad accounts that will become work for her later. Unfortunately, this has the side effect of making her a tenacious gatekeeper related to allowing new customers in the door. She leads the company's sales prevention efforts. The credit crisis and failure of established banks only validated her restrictive worldview. The salespeople view the whole new account experience akin to negotiating with Jabba the Hutt. And she doesn't tolerate arguments about the real risk being low as the product is only a download whose cost is too cheap to meter.

4. The Time Traveling Middle Manager/

Always ready to visit in your office and spend some time, he is packed with insightful commentary, nay advice, related to everything that HAS BEEN done by you or anyone else. If you had that advice AND a time machine, you would really have something. But you don't have a time machine. And neither does he. Now he's in your office critiquing the execution of your recent launch/project/product, but, you can't repay the favor because there's nothing to talk about. He has never done anything as he sees himself as the start up's conscience. His job is to observe, to comment and to offer advice.

He isn't here to do anything.

5. The Triathlete Production Assistant

She arrives at the Monday morning staff meeting to describe an extreme fitness weekend which included a 48 hour race with running, swimming and cycling. She got almost no sleep at all. She looks ok. And she will be fine for the next couple of hours. Then she begins to fade. Completely fade.

Guess what, she's tired and she hurt her ankle. She will be out tomorrow at the doctor and for the rest of week keeping off her ankle. She can't work from home because of the muscle relaxers and as she says -"The doctor says if I don't stay off my ankle this week, I won't be ready for this weekend's '72 Hour Race to Exhaustion' and I have been training for that for months".

All the while, our uber fit production assistant looks askance at her ultra unfit co-workers who may miss a day here and there over some unwise drinking decisions at Monday Night Football. Those unfit, cigarette smoking, fried chicken -pizza-junk food loving folks who have better attendance if not a healthier lifestyle.

6. The Project Manager

It can be dis-spiriting to create fabulous GANTT charts for unfabulous goals. All the start up organization's dysfunction in a walking, talking person. He is characterized by his unanswerable questions --"How can the developers lose more than one week in their completion date, when only one week has passed?" or "Couldn't we have known that people will take off work on Christmas day? or "Why does our one and only Q.A. staff need a month notice when they're going to test the company's only product?"

All this planning and effort to rise above the simple challenge that the job should take 15 people and there are only 5 available to do it.