How to be an effective early stage employee. Hint: be helpful.

daniel debow
Published in
5 min readJan 10, 2017


My first job was working for David Ossip at Workbrain. David used to jokingly call me GPSG: General Purpose Smart Guy. I was young, I was inexperienced, but I was hungry to learn. In that first role, through lots of mistakes (and some successes), I learned how to be an effective early stage employee.

I was reminded of this last year, when Scott Stirrett asked me to give a talk to his 2016 class from Venture for Canada. Venture for Canada is a nonprofit which prepares new grads for placement at startups. I’ve been working in and with startups for my entire career. I’ve learned that a startup leader has an endless stream of problems to solve as they iterate and learn how to achieve product/market fit and growth. The CEO can’t solve every problem. That’s where a GPSG (the last G can be guy or gal) can really add value.

I constantly encounter young, sharp people working at growing tech companies who want to know how to maximize their impact. So my talk was about how becoming a GPSG should be their driving goal. This really boils down to the question, “How can you give and get the most value from your first job?”

At Workbrain I started to figure out the answer to this question. Roger Martin, Dean of my MBA program offered a very useful framework in his book “The Responsibility Virus”. I’ve modified it slightly, and call it the “Helpful Hierarchy.” It looks like this:

The Helpful Hierarchy

Level 1 is when you tell your boss there is a problem. Then you walk away, leaving them to deal with it. That’s the bottom of the hierarchy. It’s the least helpful thing you can do. Your boss probably knows about the problem already. Even if they don’t, they already have 30 other problems to solve. This is no help at all. Indeed, it is un-helpful — you are just raising the stress level of an already stressed leader.

Let’s use an example: you’ve signed on a new client. (A GPSG is also a salesperson.) At Level 1, you would tell your boss you’re short-staffed for this project and walk away. “We don’t have enough capacity!”.

Then there’s Level 2: you tell your boss you’ve found a problem and investigated some causes. So you’ve taken some initiative to do some research. This is slightly more helpful but it’s not great. You’re still dumping the problem in your boss’ lap.

Using our example, this is when you’d inform your boss his job posting for a customer success team hasn’t been getting great results.

Level 3, you say to your boss, “Here’s the problem, here are some possible causes, and here are some possible solutions.” But then you leave it to your boss to decide which solution to go with. NO! Don’t stop there! 3 out of 5 is only the median point!

In our scenario, this is where you’d suggest that your boss either hire a recruiting agency or rewrite the posting.

Level 4 is: “Here’s the problem, here’s what I think caused it, here are some possible solutions, and here’s the solution I think we should pick.” Ok, you’re getting better. However, Level 4 is the minimum you should strive for.

For our example, this level is where you’d tell your boss he should rewrite the posting.

Level 5 is where you really want to be. This is where you say to your boss, “I identified a problem, figured out what caused it, researched how to fix it, and I fixed it. Just wanted to keep you in the loop.” The top of the hierarchy is where you can be most helpful.

Getting here takes a lot of courage and judgment, and those are hard skills to develop. Most new, young employees are more comfortable being told what to do. Heck, even experienced people can be uncomfortable making and acting on decisions themselves.

As a Level 5 GPSG, you would rewrite the posting, post it on more sites, and review the resumes. Then you loop in your boss to tell him you’ll take care of pre-screening and arranging interviews with viable candidates.

You’re not always going to get it right working at Level 5. In fact, you’re bound to have a lot of screwups, especially at the beginning. So be aware of the rest of your team: Who is better qualified than you? Who can you ask for help?

In our example, going right to Level 5 could mean you’re stepping on toes. Maybe you should rewrite the posting and ask someone to review it first. And if there’s another GPSG thinking like you, you’ll be duplicating effort, so communicate your plan. This is where you have to rely on judgment and know when to work as a team versus as an individual. But over time, you’ll get the experience and confidence you need to make those judgment calls.

So my advice to all employees, but especially the new ones, is to really strive to achieve Levels 4 and 5. For a long time, it will be something you have to very consciously work at. So put a sticky note on your computer, put a daily task in your calendar, partner with a colleague to remind each other. Do whatever you need to do to make this your instinctive reaction to a problem.

And for the managers, give your employees the freedom to act at Level 5. Help them hone their judgment so they make the right calls most of the time. Your company will be much more successful because you’ll have a self-sufficient workforce. This means relinquishing some control. And importantly, it means forgiving small (even sometime big) screw-ups. I know this isn’t easy to do, especially if you’re a GPSG yourself. I know I’ve told off employees who took initiative because I focused on the poor outcome rather than the good intention. We’re all human, and knowing when to give or assert control is a hard challenge, but it’s really valuable to achieve that balance. To make it part of your routine, set a reminder for yourself, just like your employees are doing. The difference is that your reminder will say, “My employees don’t exist to be my order takers.”

P.S. I’m working on a new company called Helpful. Go here to learn more about it.



daniel debow

Dad of 4, CEO of, ex-Salesforce SVP, founding team at Rypple & Workbrain, angel investor, bass player, adjunct prof @UofTLaw and curious person.