Know when to hold ’em, know when to fold ’em: How business is like poker

I love poker. If I was ever going to give up writing, it would be to do just one thing: Be a professional poker player. I’ve read the books. I watch any poker game being aired. I have a room in my house that will (very shortly, but not soon enough) contain a poker table. If you can’t find me at the computer, you’ll find me at my poker table.

My grandfather taught me to play when I was very young. In grade school, my mom ran a sort-of after-school babysitting service and I taught the other kids how to play and we’d play with Monopoly money. In college, and shortly after, I had a regular Wednesday night game. I still get to play on occasion but I never get to play as much as I’d like to.

Recently, I took a gamble on a new client and it paid off, which made me think about the relationship between poker and business. Here are some business observations inspired from poker play:

  • You are dealt a hand of talent. Some people are dealt better hands than others; just do the best you can with what you’ve got.
  • Realize that you can’t play every hand out there. You’ve got to pick and choose which one to play by sizing up the competition each and every time. Some people with better hands will beat you. Other people with better hands will make bad plays. Some will bluff and lose.
  • The hand you’re dealt is only part of the cards in play. Remember that the flop (the cards on the table that everyone sees) could change everything.
  • It’s okay to bluff once in a while. Don’t bluff all the time. And, if someone calls your bluff, be prepared for the consequences. But sometimes a little bluffing is necessary. In the business world, the term is: “Fake it ’til you make it.”
  • You have to play if you want a chance to win. I meet a lot of people who want to be entrepreneurs. They have some talent to get into the game but they lack the courage to make a bet. If you want to win you have to play and you have to be prepared to lose.
  • There is some give-and-take. It’s not all about income; you need to pay out some money (the ante, the bets, the raises) to make money.
  • The best players play a strong, aggressive game when they have a good hand and they get out fast when they have a bad hand. On the other hand, weaker players (and the entrepreneurs who will eventually tank their business) are the ones who will play through every hand even if they know they can’t win it.
  • Every hand is a gamble. It’s a risk and a single hand can swing the entire game.

So, how can you be a better business owner? By becoming a better poker player. Here is my advice:

  1. Get in the game. Stop sitting on the sidelines and watching. You might lose sometimes, and make sure you learn something every time you lose, but you might win some, too. And the longer you’re in the game, the better you’ll get.
  2. Think clearly and carefully about the hand you’re dealt. Does it have a chance to win in this round? If not, get out.
  3. Learn to take smart risks. Figure out what a smart risk is for you (how much are you willing to lose? How much do you want to win?) and make those plays.
  4. Learn everything you can about your opponents. Learn their strengths and avoid them. Learn their weaknesses and exploit them

Poker and business are very similar: They’re studies in money-making through opponent evaluation and risk acceptance. I love writing and I love the “game” of business.

How do you play?

[Photo credit: chrischappelear]

Tame the paper dragon when technical writing

I’ve been working on a huge technical writing project for a client. They expect to start rolling some of my work out to their staff and partners between November 2010 and March 2011. They have thousands of pages of supporting documents that go back at least 4 years. So,  for the next few months, I’m trying to make sense of it all while I turn it into something useful.

I’ve been swimming in a flood of paper: Reading, sorting, and mapping it out. And recently I was asked by three different people, “What’s your process of turning a great big pile of unsorted guidelines, case studies, and marketing documents into a comprehensive, user-friendly, step-by-step document that someone can follow?” I thought it might make an interesting blog post.

So here’s a generalized version of my technical writing process:

  1. One of the first things you need to do is figure out who the end user is going to be and what they are supposed to accomplish as a result of this project. From branch operations to CRM systems to selling a specific product, each technical writing project I’ve worked on had an end user who was supposed to achieve an end state. So find out what it is. It also helps to try and figure out what their motivations are (will they accept the changes or resist them?) because you can shape your work according to their level of alignment with the purposes of the content.
  2. Get a high level view of the project, review the business case, and review some of the material to get a feel for what you’re facing.
  3. Now here’s the secret ingredient and this step will make all the difference for you: Start mapping out an ideal future pathway or methodology that you will be writing to. These are the steps in the process that people will be taking to achieve the end goal. Each step in your work will probably be a major point in the step-by-step instructions you’re writing.
  4. Build out a similar “current” pathway so you can outline how the process is done today and can compare the two.
  5. Now start reading all of that reading material in-depth. Assign a code to each document and then look at your process map (in step 3) and see if you can find a place for the document on that map. If you can, great. If you can’t decide if it a good reference material. Chances are, if it can’t be tied to one of the steps on your process map and if it won’t make a good reference then it should be discarded.
  6. As you build your map, write in the names of people who can help or reference sites to obtain more information.
  7. Below each point, start fleshing out subpoints, steps, or tasks, and arrange them in order within each point.

By now, you should have a big piece of paper (or, more likely, a Word document or several pieces of paper taped together) that captures the information of the entire solution.

File those documents into some kind of order. Put the discards in a discard file (and keep them until the project is published). Put the rest of the documents into coded files that align with the steps in your process map.

And now you can start writing, interviewing, and continuing with research. Of course, all good technical writing is iterative and collaborative so expect to get back to earlier steps and make adjustments as necessary.

[Photo credit: epSos.de]

What to do if your prospects say “no”

A sale happens when you convert a prospect into a customer. But not all prospects convert. Some prospects say “no” (or they simply decline to buy or they abandon their shopping carts, depending on your sales funnel). You shift your focus to those who have said yes and you serve them to get them to buy again. Good idea.

But what do you do with the other prospects? With the ones who say “no”? Here are some ideas:

  • Build a relationship with them. Take an interest in them. Follow them on Twitter, read their blogs, listen closely to them. Invest time in them as research into the mind of people who DON’T want your services.
  • Look for common points among them to see why you are missing the mark. If they share a similarity, you can augment your existing product or create a new product to better serve them.
  • Test different products – at lower price points or with different elements – and see what they buy. Don’t offer these products to everyone, just to the ones who said “no” the first time.
  • Partner with another vendor who might be better able to provide a solution to their problem. Don’t just refer them; arrange an affiliate relationship so you can still profit from the ones who say no.
  • Ask to put them on your newsletter or ezine list.
  • Better yet, create a special “no” list that gets extra special treatment with plenty of high-value information and free samples.
  • Get their contact information and revisit them a few weeks or months down the road. (I have several clients who started working with me after initially turning me down… they found another writer, weren’t as happy as they thought they’d be, and my email or call prompted them to reconsider my services).
  • Stay positive, stay available, and invite them to contact you at any time. You never know: Their needs might change in the very near future.

While your customers are great to have, your “no” prospects can teach you so much about why people don’t buy… and they will often be the vocal minority to a much larger group of people who didn’t even bother going through the process to get to the prospect stage.

Well that’s just a slap in the face

Just two weeks ago I wrote series of blogs about how real estate professionals SHOULDN’T market themselves. I mentioned the 5 really big problems were: Offering a free home evaluation, using “great service” as a differentiator”, using schtick in place of real value, guaranteeing a home sale, and marketing themselves to locals as being experts in the city.

And then this letter came in the mail yesterday…


It was basically just a slap in the face to a few of the things I’d just talked about.

So let’s dissect this ad further:

In the above picture the real estate professional lists some accreditation and awards. Unfortunately, he doesn’t tell us what these awards are for. I’m sure they’re for something (homes sold? years in the biz? income earned?) it would be helpful to know.


Next he lists the big slap-in-the-face: “Local Knowledge” as if that’s the reason we hire real estate professionals. As if, the fact that we own a house in this area isn’t proof enough that I have my own local knowledge. Also, I’m not so sure about the use of the term “intimate”. I know what he’s getting at — in-depth, no-stone-unturned — but intimate has another meaning and it’s a little disconcerting to suggest that he has intimate knowledge of the area. Yikes!


This section had some promise… except that he uses “your” and “our” a little too much which sets up the ad to be more adversarial. He’s trying to align himself with the reader (“our area”) but the use of “your” and “our” in such close proximity makes for a less clear reading of this section.


This is a WEAK paragraph! First, there’s the market evaluation, which is another slap in the face to me. Also, being “in the position” to do something reminds me of my days in sales when we were encouraged to say: “I’m in a position to give you a great deal on…” in order to make the customer feel like they are getting something exclusive. (They weren’t). His proximity doesn’t give him “the position” to do anything different than any other real estate professional… and his market evaluation won’t be any different than those who don’t live and work in the area. And I hate to break this to him but he has access to the same information that every other real estate professional has.


This paragraph is also weak (although to his credit, he does live in the area — I checked). Referencing “the local community clubs” and “the local schools” makes it seem too generic. There are several schools and a couple of community clubs. A specific reference to at least one of those would have made this letter feel far more authentic. And again with the local knowledge reference!

If he really wants to plug his local knowledge, he should stop saying “local knowledge and instead say something like: “I’ll show you the 3 BEST streets to buy in East Kildonan” [thats the area of town we live in] “if you want to increase your home value 50% in the next 2 years, and I’ll show you the best deal on the most unbelievable pizza you’ve ever eaten!” Or, “if you have kids under 12, I know of the perfect location to buy so that they are only 5 minutes from John de Graff School”.