5 Mistakes Sales Team Leaders Make

It’s goes without saying that sales is tantamount to a business’ success. With that said, it’s surprising to see how few entrepreneurs truly commit to building a sales team. They may hire and spend in sales, but that’s different than committing, focusing and building a successful sales organization. Here’s the biggest mistakes business’ make.

  1. Not training the sales team. The first two media sales jobs I had, I received a combined total of 0 hours of sales training. 5 years earlier, I was hired for my first sales job in biotechnology. As part of the training, the new hires went through 3 days of sales training. I also spent a week each with my manager and the former territory manager doing ride alongs. Throughout the year, we received additional training in all aspects of sales. If you search “sales” on Amazon, there are 13,863 books written on sales. How many have you and your team read? If you plan on investing in building a sales team, make the commitment to training them properly and giving them the resources to succeed. There’s better access to sales resources now more than ever with sales seminars, online sales training, sales sites and blogs and books. As a starting point, subscribe to Hubspot’s Sales blog. They write and feature guest post author’s on 5 blogs posts per day.
  2. Not committing to sales. Sales isn’t something the sales team does. Sales is something everyone at the company does, especially the CEO and the executives. At one of the media companies I worked for, the CEO was getting coffee with the head of marketing of a major movie studio that I worked with. He asked if I should bring anything up in the meeting. I suggested talking about how we could help them market their upcoming releases. He replied he didn’t want to sound too salesy. Unless your business is pre-revenue, the number one job of the CEO is driving revenue. As a CEO, president, or executive you should intricately understand how the sales team operates, it’s pain points and how you can take steps to help resolve them. If there’s anything they need you can do, you need to do it. Get to know all the sales people. Personally congratulate them on progress and deals won.
  3. Not providing resources. Sales people should have one job: to sell. They shouldn’t be doing project management or be involved in onerous account management responsibilities. Those are the responsibilities of project managers and account managers. You should set up your sales team so when a deal closes, s/he can cc the corresponding staff and go back to selling. Both media sales jobs I had handicapped my ability to sell by not having any support staff. Both companies had the mentality that we’re start ups, and we’re resource strapped. Save money on air conditioning, not by not having the right sales resources. The more time you team has to sell, the more sales they’ll be doing.
  4. Not providing tools. Give your sellers everything they need. Our team uses and invests in the following sales tools: Clearslide, Followup.cc, Dropbox, Uber Conference, Join.me, CRM among others. We spend over $200 per month per sales person on tools to enable them to streamline their work flow and better do their jobs. It’s an investment I would estimate pays off 10x. When you’re evaluating a new tool, the question you should be asking is not can I afford this, but how big an ROI will this tool drive, how much easier will it enable my sellers to do their job.
  5. Not experiencing their process. It’s easy to set goals. I had a CRO who set goals based on what the board wanted and not all realistic to what the sales team was experiencing. In my first month on the job, he assigned me $50K target for the month, even though the sales cycle was a minimum of 3 months. Only a single member of the team would regularly meet his goal, the CRO would threaten the whole team by stating that the missed revenue would be pushed onto our later monthly targets of the year so it would be harder to hit the sales targets. When we would bring up challenges we were facing, he suggested we needed to “get creative” instead of offering any concrete solutions of his own. For one account, he suggested that I catch the contact in his company’s parking lot. I don’t need to explain why that’s a bad idea. This was for a reputable, highly funded start up. If you’re leading a sales team, you need to experience their pain points first hand. You need to be honest about the process and not just set arbitrary goals. They should be realistic goals, and not a way to blame the sales team for not delivering. If more than half your team isn’t exceeding their targets, you’re to blame, not them.

How to Fail

There’s a lot written these days about failing forward and failing fast. That’s nice if you’re Facebook, you’re growing faster than you can keep up and your failures are forgotten faster than they’re created. But failure for small entrepreneurs tends to be painful. Most entrepreneurs want not to fail.

Failure is what most people fear most about jumping into entrepreneurship. Embracing entrepreneurship is in a way embracing failure. They’re tied at the hip. The perception is likely that the most successful entrepreneurs are the ones who’ve failed the fewest times or not really failed at all. It’s the opposite. The most successful entrepreneurs have failed more times than they care to count or mention.

Think of Facebook’s big and yet now forgotten failures. There was Wirehog, an early peer-to-peer, file-sharing prototype that Mark Zuckerberg developed and took seriously enough to talk to investors about. This may not seem like much of a failure, but consider the fact that developing Wirehog likely took thousands of precious hours of Mark and his team’s time, time he could have spend on Facebook, a company now worth $247B!

Other notable failures of Facebook’s include Beacon, a service so disastrous, Facebook had to pull the plug after a few weeks. Developing Beacon likely took thousands of hours of engineer’s time. There was Facebook’s Poke, their Snapchat competitor; the Facebook phone; and Facebook classifieds. They all sound ridiculous now.

Facebook succeeds because they fail. With each of these failures, Facebook was pushing the envelope and evolving their platform into new spaces. The companies that aren’t evolving are the ones that are truly failing.

When I first decided I wanted to start a company more than 10 years ago, I came up with a concept, worked with designers and spent hours and hours ideating on it. I’d talk about the idea with friends who were all excited about it. It came down to committing the capital to proceed with the first order. I had the money for the first order, but struggled to pull the trigger. The (pseudo) company died a quiet death. I just stopped talking about it. Months later, I’d run into friends who excitedly would ask how the product was doing. I’d regrettably tell them I never ended up ordering the product. I didn’t learn much through the process, except on how to ideate.

Entrepreneurship isn’t about ideating, it’s about taking risk, taking action and moving projects forward. I was a classic wantrepreneur. I hadn’t even failed correctly. You don’t learn by ideating, you learn by testing and shipping a product. Get it out there.

There are some important things to understand about failure.

Failure is the process. Look to the most successful companies and see how they manage their failures. If Facebook didn’t allow itself to fail, it wouldn’t be allowing itself to innovate and lead. If you’re trying to avoid failure at all costs then you aren’t doing the right things to best enable success.

Learn, reframe, rebound and pivot from your failures.  Don’t bury your failure immediately. The only true failures are the ones you don’t learn from. Analyze the failure. Look at your assumptions, at your model, at your product, at every step to see what you could have done differently or better. In every case, you can’t know everything and most of the time the only way to know if there’s demand for a product, service, idea is to create and ship it.

Own your failure. With a failure, the tendency will be to hide it. Or even worse, by not giving it enough commitment capital to succeed in the first place. We live in an amazing country at an amazing time. Entrepreneurs are held in high esteem. Fail publicly, fail loudly, and tout your failure. Brag about it, wear it as a badge. That will cure the shame. You’ve got the balls that millions of people don’t. Everyone has an idea for a product or business, only a handful but that idea into motion and commit to it. Wear that badge proudly. Make it the best damn failure anyone’s seen.

The 5 Must Read Books for an Aspiring Entrepreneur

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In Mark Cuban’s autobiography, he talked about getting started out and reading voraciously anything and everything related to his field, business, marketing, etc. He used to read software manuals cover to cover. Drew Houston of Dropbox used to spend every weekend, reading all day long “Every weekend, I would take this folding chair up to the roof with all these books I got on Amazon. I would just sit there and read all of them. I would spend the whole weekend just reading, reading, reading.” 

Nothing prepares you for entrepreneurship like reading everything you can get your hands on. Here are some good places to start.

Richard Branson: Like a Virgin

Richard Branson’s autobiography is a fascinating look at one of the most dynamic entrepreneurs of our time.

Peter Thiel: Zero to One

When you’re just getting started, it’s important to be and stay inspired. Few books will make you want to change the world and business like Peter Thiel’s Zero to One. Peter Thiel was one of the founders of PayPal and the first investor in Facebook. He’s knows a thing or two about business and ideas that change the world.

James Altrucher: Choose Yourself

James Altrucher has seen it all. He’ll recount often how he lost millions and his shirt on several occasions. And through it, he’s gain remarkable insight. Choose Yourself will change the way you think of business and yourself. Somehow it’s only $0.99 on Amazon. It’s a quick read, get it.

Mark Cuban: How to Win at the Sport of Business

Mark Cuban is loud, brash and unapologetic. He didn’t get lucky becoming a billionaire. Broadcast.com was his third successful business. That’s a habit. His autobiography breaks it down and shows his remarkable prescient about the growth of technology and exactly how hard he was willing to work to win.

Steve Chandler: Wealth Warrior

Wealth Warrior incorporates a huge amount on wisdom about business and personal development in very few pages. A brilliant read. Steve Chandler’s focus on oneself and your motives, refocuses the whole narrative on entrepreneurship.

What are your must read books for a new or aspiring entrepreneur?

The Number 1 Rule for Entrepreneurship

A few years ago, I interviewed at Google. The interview process was lengthy and had a very corporate feel. I interviewed with everyone on the team, typical corporate stuff. Then the divisions heads came in and asked the hard questions.

A fews year prior, I had tried my stint at Wantrepreneurship. A friend and I had written a business plan, drafted a product document, and started pitching a business. There’s a huge difference from pitching a business and running a business. I think one of us even called ourselves CEO. At the Google interview, someone asked me what my greatest lesson from running a business was. I stumbled a bit and gave a half hearted answer because I didn’t have a good answer. I hadn’t run a real business.

What I know now from running my own business for three years is: the most important lesson is to get up every day, push aside all the distractions, and move the goddamn business forward, every single day. Do something, make a call, send an email, make a connection, send a pitch, follow up with prospects that guarantees you’ll be in business in a day, a month, a year. How do you know what to do? Tim Ferriss’ approach is to do the three things you most don’t want to do, first thing in the AM before doing anything else. Those tend to be some of the most important tasks. Everything else is secondary. Do it whichever way you can. It doesn’t have to be pretty, it doesn’t have to happen at 9 AM, you don’t have to play any politics and the best part is you don’t have to ask anyone’s permission. Just get it done.

You’ll find someone to take care of the accounting, the website is good enough for now, you can blog when you’ve closed more deals this month, put aside the potential pretty sounding business partnership, stop tweaking the business model and pitch deck and get some customers! You want to impress investors, get someone to pay for what services or platform you provide. Lose track of this rule, and you will get swamped in the incidentals that you might confuse as essentials. Do it enough days in a row, and you’ll be risking the business.

As Mark Cuban says, “Sales solves all problems.” Get out and sell like your life (or business) depends on it. It does. If you take that attitude, you’ll find a way to drive in revenue. If you’re not careful, busy work and distractions  will suck up your life and destroy your business. If you don’t run a business, taking this approach will help drive your career forward as well.

When Opportunity Comes Calling

“Fortune favors the prepared mind” – Linus Pauling

I recently wrote an answer to the Quora question: What is the Most Effective Yet Efficient Way to Get Rich. See the original answer here. The response has blown up, and I’ve been flattered by the comments and votes it’s received (over 3K and counting!). My previous most upvoted answer on Quora was the story of how I got Dengue Fever in Thailand under the question: What’s the Stupidest Thing You’ve Done.

It’s inspired me to start writing again for my blog and given me a new sense of direction for the content.

Many people have been struck by the answer in the same way that I was when I first read the anecdote of the Italian billionaire. It can be that simple. I was talking with a friend from France about entrepreneurship here vs France and asked him what the difference was. He said that in France when you bring up the idea that you want to start a company, people tell you it’s a bad idea, that it’s too hard and that it won’t work, but here when you bring up the idea of starting a company, people tell you it’s a great idea, that you should go for it and suggest ways they can help or people you should talk to.

My former boss whom I mentioned in the Quora answer, started his own Biotech company. Know what he did before he raised $10M to start his own Biotech company? He was a pharmaceutical sales rep. Know what he did before that? He was a Baptist Minister. And before that? He was a limo driver.

What’s even better, he met the investor who gave him $10M, waiting in line to buy tickets to a concert.

I remember Bob telling me this story and being blown away. We live in a country with a $14 trillion economy. Trillion. That’s dizzying number. Want a piece of it? It’s out there for you. You don’t have to take it from anyone. It’s sitting out there waiting to be claimed. Your keys to the kingdom are waiting on an answer on Quora or with the guy you wouldn’t think twice of in the line next to you in the ticket line for a concert. There’s opportunity around you, all the time.