How To Sell YUGE Deals











Is your sales team ready to learn how to gold mine?



The Biggest Challenge in Sales: The Unknown

I was conducting a coaching session yesterday with a sales rep in one of my client accounts. He’s relatively new to sales, having transitioned from the customer side to the supplier side, but he’s learning fast. After guiding him through some opportunity reviews, I asked him to share his perspective on the toughest challenge he’s identified as a professional seller. He said, “It’s the uneasy feeling of not knowing.”

Having spent my career in sales, I had to agree. But I wanted him to know that he didn’t have to dangle in the wind as often as he was.

Here are the top three tactics I shared with him for reducing the unknown:

1. Anticipate the problem. I suggest something I call “conditional access”. If you’ve ever engaged a high level stakeholder who acknowledges a need but wants to hand you off to a lower level contact to validate your offering, this is a valuable tactic. When they suggest you continue the dialog with one of their underlings, acknowledge the direction, but ask for access back if something should go awry. Then document it in your email recap. I’ve never been turned down on the request, and have enjoyed the benefit on the occasion I’ve had to call the higher level contact when my calls were not being returned at a lower level. Many times it’s a matter of reinforcing the sense of urgency from the leader, which is more powerful if it comes from their lips.


During a contentious telephone call with a rude purchasing agent a few years ago, I acknowledged that we had reached an impasse and suggested we call the General Manager that initiated the discussion with me. The purchasing agent actually said she didn’t think he’d take my call. She was completely caught off guard when I added him into the call, and became very compliant after he reinforced how important it was to get the contracts sorted out that day. Had I not lined up the conditional access beforehand, the alternative would have been to spend a couple of weeks leaving voicemails for the purchasing agent who would have happily watched me sweat until I met her demands.

 2. Confirm, confirm, confirm. Confirm the problem set in writing after your first dialog. Confirm the value proposition in terms of the cost of not making a decision in writing. Confirm the evaluation process in writing. Confirm every agreement you make along the way. If your contact goes quiet or won’t share some information that you need to understand the buying process more clearly, recall one of the agreements to refresh their memory on the priority of the initiative.

One of my sales methodology students, a sales representative at Cisco, shared the results of this tactic. Near the end of particularly harrowing quarter, the point of contact for his most important opportunity said they were going to delay the purchase until the next quarter simply because they had too much going on. He nodded his head in disappointment, and said, “ok, I understand, but I can’t get this picture out of my head.” He piqued the buyer’s curiosity, because the buyer asked, “what picture?” The Cisco rep replied, “I have this picture in my head of you rolling a wheel barrel full of cash out into the parking lot, dumping it over, and setting it on fire. You told me that you were burning way too much money supporting a constantly failing network.” The contact nodded his head at the reminder and placed the order that day.

3. Fan out. If you find yourself selling to one set of stakeholders, say IT for instance, and you convince yourself they are the right people since they have the budget, have purchased something similar before, and have demonstrated interest, your setting yourself up for the queasy feeling of the unknown sometime in the future. The point is, they can become easily distracted by the fire fight of the day, and they are probably buying your solution to satisfy their customer, another set of internal stakeholders.

When the phone calls go unanswered, your best bet is to have already made friends with the stakeholders on the business side of the house. If they have a vested stake in your solution, they are most likely to give you some timely insight or rattle a door if asked.

Also, if the infrastructure contact wants to keep the order size small due to budget constraints, a well-placed supporter on the business side can probably fatten the budget with other discretionary funds. Keep in mind most IT organizations get 1-2% of the company budget, while General & Administration (including marketing and sales) get upwards of the 50% of the budget.

In summary, the learning opportunity is to plan ahead for the uneasy silence. Everyone gets distracted, most people find it easier not to reply than having an awkward conversation when the situation changes, and most IT people adjust to a tight budget by squeezing the seller, not the end customer who would rather have the proper solution. Incorporate the conditional access, confirmation habit and fanning out as a daily practice and you should see the number of unknowns diminish and your forecast accuracy improve.

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I Dare You To Make A Mountain Out Of A Mole Hill! You’ll Sell More

Imagine walking in to a bank to deposit a check. As you enter the building, you notice several customers lying face down with their hands on the back of their heads. The teller is standing behind the counter, wide eyed, and nervously asks, “Can I help you?”

Do you:

  1. Continue walking to the teller kiosk to finish your transaction, silently rejoicing about the lack of a line?
  2. Assume it’s an earthquake drill, drop on the floor and place your hands over your head until notified the drill is over?
  3. Turn around like you forgot something, proceed to your car, and call the police from a safe distance?

I see sellers encounter an analogy of this situation every day. The I.T. group in a company reaches out and informs a sales representative they’re interested in adding more users, upgrading with an add on product, or replacing their current solution supplied by a competitor of the seller. They also usually request a detailed quote.

Do you:

  1. Take charge by suggesting a demo to start the conversation, agree to a lengthy evaluation, and add an “upside” item on your forecast? (See “A” above.)
  2. Send the quote and follow up later? (See “B” above.)
  3. Ask “Why, Why, Why?[1]” Do some research about their business issues, looking for a way to create a larger opportunity and justify the purchase in the face of internal competitive uses of funds? (See “C” above.)

After conducting countless opportunity reviews with dozens of technology companies, I’m pretty certain most overlook option “C”. The most common answer I hear when I ask about their prospect’s current Business Issue is some variation of “They need a new product.” This indicates to me, either a) they don’t know what a business issue is or how it impacts buying decisions, b) don’t know how to uncover and identify a business issue, c) haven’t bothered to check and just fill in some dribble to provide an answer when asked, or d) all of the above.

Let’s start with the premise it’s worth your time and energy to find the current business issues capturing the attention of your customer’s senior management. The business issues drive buying behaviors, prioritize one potential purchase over another, increase the scale of purchases, facilitate access to more powerful stakeholders, and compel faster decisions, among other things.

Every, and I mean, every, company has business issues that have the attention of senior management. It might be a focus on cost management as a result of investor pressure. It could be a merger integration that’s not meeting expectations. Product delays due to broken processes. Revenue declines in the face of a changing competitive landscape. Scaling challenges as the result of unbridled success. Or, a handful of other positive or negative issues that can be leveraged to improve the perception of your strategic contribution, create a larger opportunity, or fuel a faster purchase. I check my own perception of a business issue by asking myself, would their CEO talk about this in his/her staff meeting? I can be reasonably certain there have not been many CEO’s who ask their e-staff, “do you think we need more <insert your solution> for the staff?”

The point is, continuing on without stepping back to assess the current business issues and connecting our solution to their business issues, puts us at greater risk for a long sales cycle, a no decision due to funding a seemingly more important initiative, or a smaller pilot purchase. Conversely, if we do integrate the potential impact of addressing their most important business issue into our messaging, we have significant upside for a larger purchase, better justification to improve the sense of urgency, and broader access to stakeholders who care about addressing the issue.

So why aren’t more sales people electing to execute on “C”?

I can only think of two answers. Either, it’s because they haven’t questioned their own ingrained habits leaving them unaware, or they think the extra work doesn’t merit their time.

Assuming you, the reader, are one of these people, and you want to learn how to sell bigger deals with fewer no decision outcomes, my suggestion is to make a pact with your manager to help you break your old habits. This takes frequent review, reflection, self-assessment, feedback and a change in tactics. Ask your manager to review your most important opportunities with you on a regular basis. Strike that; demand a regular review! Ask them to challenge you on your understanding of your key prospect’s current business issues. Show them how you uncovered it, and how you confirmed it with your prospect. A change in behavior is more likely if you have to answer to someone else regarding your activities.

If you conclude that it’s more busy work and not worth the effort, I suggest you at least try it. It only takes five minutes with a computer mouse to understand the issues facing a specific company.

Let’s walk through a real life example to demonstrate how little time it takes and the information you can glean.

As I sit at my desk writing this, I look down and see a business card from a local company I’m prospecting. I use my trusty business issue finder, otherwise known as a computer mouse, and visit their website. The first thing I see is a banner announcing their intent to acquire a social media solution for their portfolio. I quickly check their latest financial reports and among positive results in bookings and revenue, they have a $17 million quarterly GAAP loss with a $46M loss year to date. Checking Wikipedia I see they have acquired four other companies in the last 18 months. This exercise took all of five minutes.

If this company was your prospect, could you incorporate the integration challenges of five acquisitions and the associated loss of $46M ytd into your pitch? If you were a senior executive in their company, would you be open to discussions with another company who said they could positively impact the integration of the acquisitions, and reduce operating costs with their solution?

Next time you think about one of your prospects, ask yourself, “so what’s the big issue?” I’m certain you’ll find something that will elevate your strategic value, improve your messaging, give you a topic to prioritize their buying initiative, and add a new dimension to your selling skills.

[1] “Why do you want to upgrade/replace/enhance/buy?” “Why is this purchase important?” “Why now?” Continuing with “why?” until you found the business issue that’s driving the request, the people who are impacted by the problem, and the urgency of the request based on the impact of not solving the business issue.




Sell Yourself: Interviewing for a Sales Job

When I graduated from college with a mechanical engineering degree, I was in for a rude surprise. Nobody was hiring mechanical engineers that year. Within my entire graduating class, only two people had offers, and both of those were with the navy.

Not one to lick my wounds, I decided to look for a job selling to engineering organizations. I answered an ad for something along these lines, which was placed by a professional recruiter. I can’t recall her name, but she taught me something that has stuck with me for decades and I’ve had the privilege to hand off to others with great success.

She taught me a six step process for interviewing. In retrospect, it’s a general sales process that could be used to sell any solution, so it might help in other ways if you’ve already landed that coveted sales job. If not, take note, and let me know how it works for you.

  1. Introduction: Begin the interview with some proven introduction skills; good eye contact, smile, firm handshake, and introduce yourself with your first and last name. You can add some rapport building chit chat, but don’t spend too much time on it.
  2. Candidate Profile: As early as you can in the discussion, and without appearing to forceful, take control by asking the interviewer to describe the characteristics of the ideal candidate. They might say things like self-motivated, easy to coach, high aptitude for learning, or any variety of key sales skills. Take notes.
  3. Sell Yourself: When they’ve completed their profile description, take each attribute identified and begin the process of describing how you have demonstrated those skills in previous situations. The examples don’t have to be sales related situations, especially if you don’t have direct sales experience. They can be from other situations. For instance, if they list leadership as a key requirement, you can describe the leadership skills you brought to your sorority or volunteer group. Give concrete examples of your exhibition of the skill where possible, or at a minimum, on your ability to learn the skill.
  4. Uncover and Address Objections: No matter how good a candidate you are, there are usually some concerns from every interviewer’s perspective. Ask them to share their reservations about you. It might sound something like, “So is there anything about my background or profile that might cause you to think I’m not the ideal candidate?” Your objective is to flush it out and address the objections. For instance, if they answer this question with something like, “well, yes, I’m concerned that you don’t have any experience in our industry”, you should empathize with their observation and then address it. Your response might sound something like, “if I were in your shoes, I’d probably think the same thing, but, I’d like to draw your attention to my SAT score. You’ll notice that I have a high aptitude for learning, and if you’ve ever read the book, “Good to Great”,  the author cites the best leaders are those with a high aptitude for learning, not industry experience.” Addressing objections takes some thinking on your feet. Its likely you can anticipate their objections for common issues like experience, education, and industry tenure. Being prepared for the objection will raise your confidence and gain theirs.
  5. Flip to the Positive: Now that you’ve addressed their objections, you want to move their focus to the positive. Ask them to identify something about you they like. It might sound like this, “so is there anything about me that you think would add positively to this job or the team?” You may hear they like your questions, your education, or your energy, etc… Your objective is to move their brain from the negative (objection) to the positive. This shift in thinking is very important for the success of the next and last step.
  6. Closure: Once you have them on the positive note, the last step is to gain their commitment to you. If they are not the hiring manager, your close may be, “so would you feel comfortable recommending me for this position?” You’re likely to get a positive answer, but if not, flush out the concern and address it as in point four above. If they are the hiring manager, you can get even more pointed in your close, “assuming you have no other candidates as promising as me, can I count on an offer?”  The sharper the close, the more likely a seasoned sales leader will appreciate it.

The first time I used this process was during a two day interview process for a software company with 25 other recent college graduate candidates in the rotation. During day one, I had nine back to back interviews with hiring managers from different sales offices around the U.S.  At the end of the day, I reluctantly informed the HR leader that I couldn’t stay for day two as I had an interview with another company out of state. She whispered to me that it wasn’t a problem since I ended up in first place on all nine hiring manager’s lists. I departed early for the other interview, but ended up accepting my first sales job from this company. The hiring manager I ended up working for later told me that I was the only person that “sold” him. The selling process was apparent in my interview dialog and it wasn’t lost on him.

I’ve shared this process with many people over the years, and every single one of them has reported positive results. Recently, my son graduated from UC Davis. During his second interview with a major software company there were multiple hiring managers on the other end of a web meeting. Halfway through, the lead manager stopped the conversation and informed my son that he had never seen so many heads nodding at the same time during a group interview. He then asked my son if he would was ready to accept a job offer on the spot. I’m happy to report I have a gainfully employed son with a career track in sales.

*** Please “like” this post or forward it to anyone you know looking for a sales job – or any job for that matter.
