How to ask for help

First of all, stop being embarrassed about asking for help.  Everyone needs help once in a while.  Some people need an intro to a prospect or a partner, others want an opinion on a project they’re working on while still more need advice on a decision they’re trying to make.  There’s literally no one that doesn’t need help at some point in their life.  So stop being ashamed of needing help.

The real question you should ask yourself is “am I giving as much as I am taking?”  That is, when people ask you for help, do you respond?  When a friend asks you for advice, do you listen?  Help isn’t a trading game.  It’s not a transaction where you give A in return for B.  Help is something you ask for when you need it and something you provide when you’re asked.  If you’re doing one but not the other, we may have a problem.

And if your answer was “I’m not really giving as much as I’m asking”, it’s not too late to change.  Go ahead, ask for help but also take the time to offer it in other places.  Help is all about paying it forward, even if your payment is a bit late.

What Are You Asking For?

The first thing to figure out is what you’re asking for.  Help needs to be specific.  You’re asking someone to do something for you and it’s up to you to make it easy for them.  So rather than asking “Hey Bob, I need help on my job search” or “hey Bob, do you know anyone”, you should do the research and ask Bob for a specific item.  It’s not Bob’s responsibility to figure out who you should talk to, it’s yours.  So for example, if I need help with a job search, I shouldn’t just ask for general help, I should say:

Hey, would you mind helping me with my job search by helping me increase my visibility?

Make it specific

Yes, I know you need three different things but if you ask for three different things I’m going to be overwhelmed.  Decide what is the most important thing you need help with and ask for that.  Don’t ask a customer to both refer you to a new prospect AND give you a testimonial.  Ask for the one thing that’s most important for you and that’s it.  When you start asking people for a list of items, they stop seeing this as a nice thing to do and start seeing it as someone trying to monopolize their time.

Again, let’s use my previous example.  Yes, I would like people to help increase my visibility for my job search but that’s too general.  What am I asking them to do?  Do I want them to talk to people about me?  Send out my resume?  These are pretty heavy duty asks and not very specific.  Let’s make things specific by adding a request:

Hey, would you mind helping me with my job search by helping me increase my visibility?  I’d really love it if you shared my previous LinkedIn article.

Why should they do this for you?

Yes, people want to help, but helping you risks their social capital.  What if Bob introduces you to their CMO friend and you ask them a bunch of nonsense questions?  That’s going to reflect poorly on Bob.  When you’re asking for help, you’re often asking people to put their own reputation on the line.  In order to do that you need to have a good reputation and you need to make it clear to them what you’re going to do with this help.  What are you going to ask this CMO that you’re being introduced to?  What are you trying to sell them?  Ultimately, if folks are going to help you they want to know that you’re worth helping.  Make sure the ask is reasonable and doesn’t risk their reputation.  For example:

Hey, would you mind helping me with my job search by helping me increase my visibility?  I’d really love it if you shared my previous LinkedIn article.  It’s a mid length post about starting a job search.  Applicable to everyone I think and with some good ideas for those just starting a job search.  I wrote it out of my own past experiences and I think it could be helpful to a wide variety of folks.

Make it easy

People love to help, but you know what they love even more?  Being lazy.  The easier you make it for them to help you, the more likely they are to do it.  You want them to introduce you to someone?  Send them an email with all the details that they can simply forward on.  Don’t ask them to craft that email themselves because they won’t.  In a similar vein, if I want people to share my previous article, it’s on me to make it easy for them to find and share it.  So:

Hey, would you mind helping me with my job search by helping me increase my visibility?  I’d really love it if you shared my previous LinkedIn article.  It’s a mid length post about starting a job search.  Applicable to everyone I think and with some good ideas for those just starting a job search.  I wrote it out of my own past experiences and I think it could be helpful to a wide variety of folks.  The article is right here.  All you need to do is take the URL and share it, preferably on LinkedIn but anywhere else works.

Thank you!

That’s all there is to it.

Oh and if you enjoyed this article, would you mind helping me with my job search by helping me increase my visibility?  I’d really love it if you shared my previous LinkedIn article.  It’s a mid length post about starting a job search.  Applicable to everyone and with some good ideas for those just starting a job search.  I wrote it out of my own past experiences and it would be helpful to a wide variety of folks.  The article is right here.  All you need to do is take the URL and share it, preferably on LinkedIn but anywhere else works.

So You Need A Job, What Now?

First, Make The Bed

I know, sounds silly but trust me it works. Right now you’re feeling like a failure, you’re stressed about money and you’re embarrassed to tell your family and friends that you’re out of work. Go, make the bed. It’s a quick and easy thing that will make you feel better. Your home will look cleaner and you will feel like at least one thing got done today.

Ok, bed done? Awesome, let’s move forward.

No spam!

First things first, don’t just start spamming applications to jobs. Let’s take some time and figure a few things out.

What are you looking for?  What’s the right job for you? Yes, I know that right now you just want a paycheck but that make you sound desperate and that lowers your odds of finding a job. So what job would you add the most value in? What industry? Role? Size of company?

What’s your story?  People are going to want to know why you’re looking, so craft a story. Keep it honest and never complain about your past job, but don’t be afraid to do some marketing for yourself and highlight your accomplishments. For example:

I’ve spent the past four years as head of technology and products at Act-On. It’s been an amazing experience for me working with a great team of product managers, engineers and my fellow execs. We’ve rebuilt the product with a services oriented architecture, replaced the outdated UI with modern interface, added a data product, moved into AWS and introduced the first piece of Act-On’s machine learning strategy.

Unfortunately, as part of the company’s effort to become cash flow positive, the decision has been made to centralize technical operations in Portland. It’s a good decision for the company and I support it wholeheartedly, but I’m not personally looking to relocate. Which means I’m working on a transition and figuring out what my next step is.

Ideally, I’d like to find a start up or midsize company to join as the head of product. Something in the B2B world I know so well, and around the 50 to 500 person size. A place that can benefit from my ability to build a team, a product and a vision.

Look at that. It tells a clear and honest story, highlights accomplishments and details the kind of position you’d be perfect for.

Your target list

Next, come up with some companies that you want to work for. This list should clearly match the kind of position you highlighted in your story above. Once you have this list, start checking on LinkedIn for who you know at those companies. Reach out to those people and see if you can catch up with them. Don’t reach out with “hey, can you get me a job?”, that’s just tacky. Reach out and genuinely try to catch up with folks. Once you’ve met, chatted, talked and caught up, then you can ask them for an intro.

Yes, do this even if the job you wanted isn’t listed as open. You never know what you’ll find and getting into an open position before it’s even advertised is perfect.

Your network

Next, start chatting with your network. Again, don’t just send out a mass email titled “hey, hire me!” No one likes getting those. Reach out to specific people, send them a personalized message and ask to catch up. Spend time with folks, be personal and real. See if there’s something you can help them with and be genuinely interested in what they’re doing. This is all basic stuff out of How To Win Friends but the bottom line is that you need to be genuinely interested in the other person if you want their help. Otherwise, you’re just that creepy guy in the back of the room handing out business cards.


What recruiters are active in your industry? Can you reach out to them? Recruiters are awesome. They’ll do the job search for you and they often have a direct line to the hiring manager.

Be public

Finally, don’t be afraid to make your job search public. There’s no shame in moving on from a job. Everyone does it at some point in their career. Rather than try to hide it, celebrate your accomplishments and let your network know you’re in the market. You never know who’s out there listening.

And on that note, if anyone is looking for a product leader, let me know, I’m looking.

What’s A Good Day For You?

I was in an uber on Thursday morning, heading from PDX to the Portland office, and the driver asked how often I come up.  When I answered “every Thursday”, he was a little amazed and said that sounded awful.  So I tried to explain to him that Thursdays were actually the best day of the week for me.

Most other days I’m usually on the phone all day or working on some presentation or document.  I rarely interact with folks directly and I don’t have many casual conversations.  Thursdays are different.  Thursdays I get to interact with my team.  Even my Thursday meetings are better since they’re usually face to face.  Thursdays are filled beginning to end with human interaction and, for me, that’s the very definition of a good day.

Now a day filled with human interactions is probably not everyone’s cup of tea but that brings me to my question; what is your definition of a good day?  And even more importantly, what can you do to make good days more common?  Do you want more interaction?  Less?  Smaller projects that can be done quicker?  Bigger projects?  More team work?  More solo work?  What is it that you can do to have more good days?

For me, the driver’s question made me realize I could have more good days just by getting out of my office and sitting somewhere near other people.  It’s such a simple change but it made a difference.

So take a moment to think about what a good day means to you and feel free to let me or your manager know how we can help make more of those.

Why Most B2B Software Implementations Fail

Business-Success-FailureMy first job out of college was building, installing and implementing software that scheduled agents in a call center.  For it’s time, this was a state of the art application.  It took into account each agent’s skills, languages spoken, times available, shift preferences and even the kind of media they preferred to handle.  All of this was factored into a scheduling engine that analyzed, optimized and came up with a schedule that could increase a call center’s efficiency by 100% or more.  So imagine my surprise when the first request from most customers during an implementation was “show us how to enter our current schedule into your system and that’s it.”

Think about that for a second.  They just spent a considerable amount of money on a state of the art system that was easy to use and much faster than anything they had before; a system that could give them 100% better results, and what they asked it to do was maintain the status quo.  That’s sort of like me telling you “I have an app here that can help you get 100% healthier in under a week.  It will analyze your exercise and eating habits, look at your preferences and dislikes and then spit out an exercise and nutrition program that you’ll enjoy and fits into your schedule. This system is easy to use and will grow with you adapting to your needs.”  Now you take this system and use it for nothing more than tracking your weight.  Crazy, right?

Except this situation repeated itself at every single company and with every single product I’ve ever built.  Each and every time we sold the customer a highly advanced system that could take what they’re doing and optimize it for much better results, and the most common response was “just show me how to use your system to do what I’m doing today”.  In some cases there were valid reasons for a certain lack of flexibility, reasons like union contracts or government regulations, but even in these situations the lack of flexibility wasn’t complete.  Yet even these customers refused to optimize within the limited constraints they had.  Every where I went the status quo was always preferred, even when presented with a tool that could make life easier.

The result?  Software implementation that were barely used and customers that were disappointed with results that never measured up to the promises they heard during the sales process.

[Read more…]

Beware The Tiger Team: Why Special Project Teams Can Sometimes Backfire

Tiger Team: noun, a team of specialists in a particular field brought together to work on specific tasks.

I’m sure you’ve heard this before:

  • “This project is stalled, let’s put a team together to kick start it”
  • “Holy crap, we really need to improve our [department x], let’s get some folks on this right away!”
  • “Wow, how did the competition beat us to this?  We need to put together a tiger team right now to solve this!”

Ahh yes, the all hands on deck speech also known as the mating call of the tiger team.

But Shouldn’t We Fix These Problems Right Away?

Now don’t get me wrong, these are indeed big problems and you should definitely get your best minds on solving them right away.  A well assembled tiger team can cut through red tape, process issues and organizational inertia like a light saber through a storm trooper.  And yes, if you have a short term problem, by all means, put together a short term team to solve it.  Still, pause a second and answer this question for me:

Seriously, if the situation is so dire, how did you let it happen?  How could things have gotten this bad without anyone noticing or addressing them?  How did your team / division / department / company row so far up the proverbial creek that now you now need to call in a hit squad of your best people just to turn you around, build you a paddle and push you back into the water?  And here in lies the issue with tiger teams.

Solving The Root Problem

Tiger teams are sexy because they’re fun to put together and execute.  Get some cool people in a room, think up some awesome solutions, cut through the mess of red tape and get things DONE!  YES!  WE’RE SAVED!  And honestly, that’s actually true.  Tiger teams can and do save the day.  The problem though is that they’re so sexy and fun and effective that many times no one bothers thinking about why things went wrong in the first place.  Why should they, the tiger team has saved us!

Except constant tiger teams are like living in constant crisis mode.  Some people thrive on it but most will eventually burn out of the continuous ebb and flow of crisis followed by tiger team followed by yet another crisis.

Tiger teams are an effective tool in our management tool kit.  They’re also a good way to solve HALF the problem.  Tiger teams solve the short term problem, what they don’t do is solve the long term issue of how we got here in the first place.  For that we need something else, something I like to call, the Human Team.

The Human Team Sounds Lame!

Yah, it does.  Tiger sounds way better.  Humans are weak bags of pink flesh.  Tigers are 500lbs of deadly muscle and claws!  Tigers tear through barriers while humans cower behind them.  All true, but let me point something out to you.  Humans rule this world and tigers need protection from us to survive.  Know why?  Because tigers are animals that can’t adapt, can’t learn and can’t change their ways.  Humans do all those things, and that’s what the Human Team is all about.

Yes, get the tiger team in place to tear through the barriers and get the job done RIGHT NOW, but also put together a human team to analyze what got us in this mess in the first place.  Should we change our ways?  In what way?  What can we learn from this?  What can we do better?  What process needs to change?  What’s the long term solution here so we never end up in this sort of crisis again?

Without the human, the tiger is going to do some damage but will eventually exhaust itself from constant fighting.  With it, it’s an short term solution that’s rarely needed but very effective when called upon.