5 Tips For Emailing CEOs

Over the years I’ve developed an approach for emailing C-level executives that has worked well for me. I thought I’d share some of that approach here. Here are 5 somewhat tactical tips:

1. Emails should be as short as Tweets. Write emails like you’re writing a Tweet. I think Outlook and Gmail should add a feature that shows a countdown from 400 for every character that you type – and if you go over 400 characters it won’t let you send the email. Unless absolutely necessary, keep your emails short enough to be read on an iPhone without scrolling.

2. Don’t worry about grammar and formalities. Marketers write perfect emails, people that do big deals don’t. Write short and quick and to the point. Here’s an example of what I mean.

Bad email: "Hi John, I’m writing to setup some time with you on Wednesday or Thursday of this week. I am participating in our company's board presentation this week and we are trying to lock down a couple of pieces of information about our potential partnership. I know that you are extremely busy, but It would be greatly appreciated if you could spare a few minutes so that we can discuss the details of our partnership. Please let me know the best way to setup a call. Kind Regards."

Better email: "Hi John, have 5 mins to chat this week? Have a board meeting coming up and need to get on the same page on two quick things. Thx."

3. Don't be afraid to resend. If you don't hear back, give it a few days. If you still don't hear back, take the initial email and forward it to the CEO and say something like, "Hi John, hope all is well. Following up on the below. Thx."

4. Make it easy to reply. If you have multiple asks in the email, separate them into multiple emails. Let them handle each email/task individually. Don’t let one task get stuck because the CEO doesn’t want to respond to the other.

5. Be their equal. Most important, write like you’re writing to a peer. Don’t be deferential. You are on equal levels. You both have something that can help the other – act like it. As I wrote a while back, don't be a salesperson.

My Interview With Yesware

Last week Jessica Stillman, a freelance writer for the Yesware Blog, contacted me to do an interview on the topic of CRM compliance. See the full interview here. One of the fundamental challenges with CRM compliance is that sales reps often don't understand why managers need them to do lots of data entry because they don’t know what managers are actually doing with the data.  The main point I made in the interview was that managers should be much more transparent on this. Not only should they show their reps how they use the data to manage their business and make good decisions and communicate what’s happening on the ground up to the board and executive team, managers should take it a step further. They should actually allow their reps present directly to the executives and/or board using reports that pull their own individual data from the CRM system.

I found that doing this is extremely empowering to reps and dramatically reduces the friction that comes from low CRM compliance.  If you find this topic interesting, I recommend checking out the full post.

Spreading Innovation

There’s a long but good Atul Gawande article in this week’s New Yorker worth reading that’s relevant to what many of us are trying to do -- spread innovation and change minds. He writes about why some new innovations spread quickly and others don’t.  Talks about the fact that doctors adopted anesthesia really quickly but it took them years and years to begin sterilizing operating rooms (arguably a more important innovation).

Talks about the critical importance of the human factor in spreading innovation – and how a simple treatment for Cholera (a mix of sugar, salt and water) never spread in Bangladesh until human beings went out on foot and sold it, door to door.  Also uses a more relevant analogy:

This is something that salespeople understand well. I once asked a pharmaceutical rep how he persuaded doctors—who are notoriously stubborn—to adopt a new medicine. Evidence is not remotely enough, he said, however strong a case you may have. You must also apply “the rule of seven touches.” Personally “touch” the doctors seven times, and they will come to know you; if they know you, they might trust you; and, if they trust you, they will change. That’s why he stocked doctors’ closets with free drug samples in person. Then he could poke his head around the corner and ask, “So how did your daughter Debbie’s soccer game go?” Eventually, this can become “Have you seen this study on our new drug? How about giving it a try?” As the rep had recognized, human interaction is the key force in overcoming resistance and speeding change.

A Simple Sales Presentation Agenda

If you need to do a sales presentation and you have no idea where to start, here's a quick agenda I put together that should get you going:

1. Who we are
2. The problem we're solving
3. How we solve it
4. Why you should believe we can solve it
5. How to get started on solving it

What A Startup Needs To Start Selling

Over the last few weeks I've been helping a CEO of a very early-stage startup with her go-to-market strategy. She's planning to hire a head of sales in the coming weeks and she asked me to brainstorm what that person should be responsible for. To me, there are two broad buckets: 1.) that person should be able to get deals done quickly and 2.) just as important, that person should create and publish process, systems, collateral and other documentation (that should continuously be iterated) that will allow the company to scale.

With #2 in mind, I put together the list below. A lot of the things on the list are required to start selling, but many of them are there to ensure that the product and positioning of the product are setup to constantly be iterated. Most successful products and new product pitches look very different than they did when the entrepreneur initially went to market. It's critical that there are systems in place that enable constant change.

Pipeline

• Lead Framework
• Build Lead List
• Segment Leads (A, B, C)
• Key Contacts at High Priority Leads (email/phone)
• Inbound Lead Management Process

Access Approach

• Script(s)
• One-Pager

Collateral/Documentation

• Presentation Deck
• Presentation Scripts/Talking Points
• Proposal Template
• References Document
• Order Form (business terms)
• Agreement (legal terms)

Sales Cycle Management

• CRM System Implementation (e.g. Salesforce.com, Excel, etc.)
• Stage Development
• Key Leading & Lagging Metrics To Track
• Leading & Lagging Metrics Targets and Timeline
• Key Reports (weekly, monthly, quarterly)

Other

• Difficult Questions (and answers)
• Cast of Characters Document (who do we care about and what do they care about?)
• Urgency Angles
• Competitive Matrix
• Qualitative Results: What works / What doesn’t (documented weekly)
• Insights/Learnings (documented weekly)

The Photocopier Effect

I've written in the past that one of the secrets to negotiating with partners or potential partners is to always communicate the reasons behind your position. It's critical. The partner doesn't have to agree with your position, but you must explain the business logic behind it. People don't like things that don't make sense. With this in mind, I came across an interesting phenomenon called the "Photocopier Effect" in a Malcolm Gladwell New Yorker article from a while back. The Photocopier Effect proves, scientifically, why it's so important to emphasize the reasons behind your position. From the column:

...Harvard social scientist Ellen Langer. Langer examined the apparently common-sense idea that if you are trying to persuade someone to do something for you, you are always better off if you provide a reason.

She went up to a group of people waiting in line to use a library copying machine and said, "Excuse me, I have five pages. May I use the Xerox machine?" Sixty per cent said yes.

Then she repeated the experiment on another group, except that she changed her request to "Excuse me, I have five pages. May I use the Xerox machine, because I'm in a rush?" Ninety-four per cent said yes.

This much sounds like common sense: if you say, "because I'm in a rush"--if you explain your need--people are willing to step aside.

But here's where the study gets interesting. Langer then did the experiment a third time, in this case replacing the specific reason with a statement of the obvious: "Excuse me, I have five pages. May I use the Xerox machine, because I have to make some copies?" The percentage who let her do so this time was almost exactly the same as the one in the previous round--ninety-three per cent.

The key to getting people to say yes, in other words, wasn't the explanation "because I'm in a rush" but merely the use of the word "because." What mattered wasn't the substance of the explanation but merely the rhetorical form--the conjunctional footprint--of an explanation.

Influence: The Psychology Of Persuasion

I just finished reading Influence, by Robert Cialdini. The book is about persuasion and examines the psychology of why people say "yes". I've never been a fan of the psychology of sales (I don't like the notion of tricking someone into buying something) but the book definitely gets you thinking. It basically walks through 6 "principles of influence". The principles are: reciprocity, scarcity, consistency, consensus, authority and liking.

The book describes each principle and gives several examples of them in action. I've included some of the more interesting examples below.

The book describes a study where people go to homes and ask if they can place a small sign in the owner's front yard promoting a charity of some kind. Then, a few weeks later, the same people come back and ask if they can put a much, much larger sign in the front yard. They find that the people that said yes to the small sign are far, far more likely to say yes to the larger sign than the average person. This is the notion of consistency -- once you know you're the kind of person that puts a sign on your front yard, you become much more likely to do so when the stakes are raised. There are some obvious applications of this in sales (e.g. small deals that turn into large deals over time).

Another study found that when you call a potential voter and ask them if they're going to vote and they say "yes", they're far more likely to actually go out and vote than they would've been had they not taken the call (again, people like to appear consistent)

Several studies have found that we are far more likely to help people that dress like us.

In one controversial Ohio political election a few years ago, a man given little chance of winning the state attorney-general race swept to victory when, shortly before the election, he changed his name to Brown—a family name of much Ohio political tradition.

Salespeople in men's suits stores will always show the customer the most expensive suit first. Because when it comes time to buy a sweater or a pair of shoes, these look very expensive when contrasted wiht the expensive suit. It turns out that when a man enters a clothing store with the express purpose of purchasing a suit, he will almost always pay more for whatever accessories he buys if he buys them after the suit purchase than before.

This principle is applied in this excerpt from the book which is a letter from a college student to her parents.

Dear Mother and Dad:

Since I left for college I have been remiss in writing and I am sorry for my thoughtlessness in not having written before. I will bring you up to date now, but before you read on, please sit down. You are not to read any further unless you are sitting down, okay? Well, then, I am getting along pretty well now.

The skull fracture and the concussion I got when I jumped out the window of my dormitory when it caught on fire shortly after my arrival here is pretty well healed now. I only spent two weeks in the hospital and now I can see almost normally and only get those sick headaches once a day. Fortunately, the fire in the dormitory, and my jump, was witnessed by an attendant at the gas station near the dorm, and he was the one who called the Fire Department and the ambulance. He also visited me in the hospital and since I had nowhere to live because of the burntout dormitory, he was kind enough to invite me to share his apartment with him. It’s really a basement room, but it’s kind of cute.

He is a very fine boy and we have fallen deeply in love and are planning to get married. We haven’t got the exact date yet, but it will be before my pregnancy begins to show. Yes, Mother and Dad, I am pregnant. I know how much you are looking forward to being grandparents and I know you will welcome the baby and give it the same love and devotion and tender care you gave me when I was a child.

The reason for the delay in our marriage is that my boyfriend has a minor infection which prevents us from passing our pre-marital blood tests and I carelessly caught it from him.

Now that I have brought you up to date, I want to tell you that there was no dormitory fire, I did not have a concussion or skull fracture, I was not in the hospital, I am not pregnant, I am not engaged, I am not infected, and there is no boyfriend. However, I am getting a “D” in American History, and an “F” in Chemistry and I want you to see those marks in their proper perspective.

Your loving daughter, Sharon

There are lots of funny and interesting examples like this throughout the book.

Influence is pretty good and definitely worth the read if you have an interest in this topic. But like most business books it's way too long. So if you only have moderate interest in this topic, I'd try to find a cliff notes version.

Research & Preparing For Meetings

When preparing for an important sales meeting, salespeople will generally do a bunch of research; they'll read news articles, read the company's 10-k, check out the LinkedIn profiles of the people in the meeting, etc. Often, they'll spend money on Hoovers or other databases to gain any edge they can. Of course there's nothing wrong with this, but one thing to consider: how often has the thing that you currently care about most at work (the thing that is going to get you a big bonus) been available in a 10-k or a press release.

Sure, directionally we know that you want to grow revenue or cuts costs or prioritize a new product launch. But I can't learn the important specifics of that in the media or in a 10-k. Further, business has become so much more iterative over the years that, in my experience, by the time the media picked up on an initiative I was working on, we were already onto the next thing.

With that in mind, I would propose that when you do research, you prioritize having conversations with people on the inside. Before a meeting, find someone you can talk to that will help you prepare. It could be a junior person, it could be a personal assistant, it could be anyone that can help you get information.

These people should be happy to talk to you. You're not having these conversations to get inside info you shouldn't have access to, you're having these conversations to make the upcoming meeting more productive.

So when preparing for a meeting, yes, do your research. But more importantly, have conversations with people on the inside that know what people on the inside care about.

Selling To CEOs

Seth Godin had a good post a couple weeks ago titled, The danger of starting at the top where he talks about the downside of selling directly to a company's CEO. They key line is this:

When making a b2b sale, the instinct is always to get into the CEO's office. If you can just get her to hear your pitch, to understand the value, to see why she should buy from or lease from or partner with or even buy you... that's the holy grail.

What do you think happens after that mythical meeting?

She asks her team.

And when the team is in the dark, you've not only blown your best shot, but you never get another chance at it.

I agree and disagree with this. Two thoughts:

1. Yes, you need to be careful when going straight to the top, but I don't think you need to be afraid of selling to the CEO directly. But you do need to be careful in your approach. In short, don't sell. Have a conversation. Ask about her business, what problems she has, talk about what you do, your industry, her industry, potential synergies, who would be good to talk to, etc. If you're not selling, you should be comfortable talking to anybody.
2. While you're having conversations, you should also be evangelizing. That is, you should be drip marketing your prospects. I defined drip marketing in earlier posts as:

Regular, short and highly interesting/engaging/insightful pieces of information (most often without an ask) that educate the recipient and — just as importantly — change their perception of what you do in a favorable way.

If you're having conversations and "dripping" the right people, you should be free to navigate your prospect's company to find the person that will be most interested in your solution.

The Downside Of Good Reporting

It turns out that, even today, nearly all of the big checks in the ad industry are still being written for big, broadcast marketing efforts (television ads, radio ads, billboards on the side of the highway, etc.).  You might find this surprising given all of the conversion-based marketing channels that have popped up over the years. Advertisers no longer have to worry about not being able to track their ad spend. Marketing has become measurable. Google can tell you how many leads they drive to you so the problem of wasted ad spend should be over. So why are marketers continuing to spend on the big, hard to measure stuff? In many cases, the reason is that lots of ad buyers are really out to do one thing: avoid getting fired. So they’re very reluctant to take a risk on something that can be tracked. Many would rather their boss see a beautiful ad on the highway on her drive to work as opposed to a report showing that the new marketing campaign failed to drive a positive ROI.

With that in mind, in your early conversations it's important to understand where your prospect sits on this topic. My take is that high performing companies and individuals want to measure their performance and the performance of their vendors -- so that they can intelligently expand (or limit) partnership growth. If they are reluctant to measure success, they may not be the right partner as growing the relationship will typically be much more difficult.

Be cognizant of the fact that your partner might be hesitant to be measured. Try to get them to open up a bit on the topic -- it'll help you get a better sense of whether or not they're the right fit.

CEO Pay

According the AFL-CIO, the average Fortune 500 CEO made $12.9 million in 2011. After taxes, that's about $430,000 per month -- or $198,000 every two weeks. CEOs at big companies get paid a lot of money -- and my sense is that the top priority for most of them is to do whatever they can to keep those checks coming.

That's an important thing to remember the next time you're asking one of them to take a big risk on your product.

B2E2B (Business to Employee to Business)

We all know b2b and b2c, and even b2b2c. I'd propose that an emerging software business model is b2e2b (business to employee to business). While it hasn't been called out clearly like this (trust me, I've 'Googled' it) there are many companies that are already using this approach (Yammer, Dropbox, Xobni and others). The way it works is that a company builds a product that can be accessed directly by a single employee of an organization. As the number of users within a company grows and reaches a critical mass, the company then has a salesperson contact the organization to make the upsell -- e.g. business to employee to business.

Of course, this model is interesting in its own right. But there are much larger implications for enterprise software. Chris Dixon and others have talked a lot about the fact that enterprise technology is far behind consumer technology. As I've written before, I believe that the reason for this is that enterprise technology can get away with being bad. For example, if you're a payroll provider and you provide a lousy interface for employees you can get away with it because you only have to sell one person in HR on your product (and then they force ten thousand people to use it). But if you're a consumer site like Mint.com you can't get away with being lousy because you have to sell 10,000 people, one by one. You have to be great or you'll fail.

And this is why the b2e2b approach is so important. It’s radically changing the way enterprise software is built and sold. And as a result, we should see the quality of enterprise technology begin to catch up with consumer technology. And when it does, those big b2b companies that continue to rely on their brand or their sales force to drive sales will begin to collapse.