An interesting question recently came up in our Sales Success Community (join our mailing list to get a free invite). I thought others might benefit from the question and the associated answers from some of the top selling guests we’ve had on the show. Feel free to add your own advice and recommendations in the comments sections below.

Ethan Asks:

I am sales dude #1 at a tech startup. The CEO is a successful consultant from Boston and wants me to take a “smile and dial” approach to sales. This is highly incongruent with my personality. I would rather take a more personalized approach. But in the face of disappointing results, his solution is to tweak the script/pitch and improve my product knowledge. I am spending my off hours improving my product and industry knowledge as well as researching prospects so that I can show him there are other ways that work better. My questions is this; have you ever had conflict with your Sales Manager/CEO, especially in regards to the sales process? If I am successful, I will be responsible for building the sales processes and the future sales/marketing team. I am given some flexibility, but guys, I’m 19 years old. I barely know what I’m doing so it’s sometimes difficult for me to have tough conversation with an accomplished consultant from Boston. Your insight and advice is appreciated!

Debe Rapson Suggests:

First question-is the solution you are selling transactional?  What is going to be the typical deal size?  If transactional (not a complex solution sell), you can go a little less personalized-volume becomes more important with a smaller deal size.

Either way, a more personalized approach which should include asking good questions about their business needs is always the best approach even for a more transactional sale, but all that being said, pick up the pace and reach out to more folks (personalized emails, calling companies that look qualified) is probably a good idea in the beginning.

Consultants aren’t sales people, that’s why they hired you and it isn’t at all surprising that you are experiencing conflict with him.  He doesn’t have full confidence in you (you are pretty inexperienced, so don’t take offense), but sounds like you’ve got the confidence to prove to him you can do it!  As soon as you start seeing success, you’ll prove yourself.

Your instincts are right on, but pick up the pace, call on companies that look qualified “on paper” and boost your industry and solution experience.  Take him out in the field with you, you’ll learn a ton and so will he.  I don’t recommend you go into sales management.  You are 19 years old, get 5 years under your belt in sales and then consider management-you are simply too inexperienced to lead a team and the likelihood of it not going well is high.  Sales is an awesome way to make money and you should spend the next 5 years honing your skills, making mistakes and learning how to be successful!

Jen Linker Recommends:

Thank you for sharing this very insightful question. Some of my friends are in similar positions to this person. They are just starting off in sales and feel really uncomfortable undertaking traditional sales approaches because it doesn’t feel natural to them—especially in a day-and-age where most people don’t even answer their phones.

My advice to this person is this. Yes, you are correct that you can be a successful sales individual and not have to pick up the phone every day. In fact, a sales individual on my floor is very successful in this approach. However, not doing a specific task because you feel uncomfortable isn’t necessarily reason enough to not do a task.

It completely makes sense why this person would feel uncomfortable picking up the phone. I felt the same way as them. Sometimes I would think how weird it was for a 20 something year-old person to sell a six figure solution to a forty-year-old CMO. But, at the end of the day, you know more about your solution/product than any other CMO, CEO, or other business person.

Although selling through the phone can be challenging, it does work. I encourage you to try it. Selling on the phone is going to feel weird at first, but once you practice enough time and fail enough times, you will eventually get into the groove of things.

My advice to you is to try it and push yourself out of your comfort zone. If you still feel the same way after a few months then you can always go back to what you were doing before. Remember, successful sales people are those that try new things and are always opening to learning.

I hope this helps!

Reid Oliver Says:

Interesting question!.. short answer from my end would be that I haven’t had a conflict like this in my short time here due to our flexibility. BUT, I see this being a common issue when it comes to quantity vs quality.

My insight here would be to try and work a blend of the two. The fact that he’s only 19 y/o without much experience makes sense that he’s not going to have very much freedom when it comes to process. If I were him I would continue to try and hit the #’s his CEO wants, but also try to incorporate a bit more personalization and reference the 1000’s of articles out there today on “why it works”. I would also record all of the wins I have and what I did specifically to get that win. Do the results look like more personaliztion= more wins?

Mike Cochrane Suggests:

This is an interesting situation and I’ve had several “back and forth” thoughts about it as I drove today. I have a question and then two comments/pieces of advice:

Question…He never mentions how he feels about the tech field in general or this company specifically. Is he passionate about the field and/or the company? This is a startup…Does he believe in the consultant that is heading up this initiative? Would he be just as happy/interested selling medical supplies, payroll systems or real estate?

Comments/Advice…Assuming the answers to my questions above are all positive, I would suggest that he do two things (one of which he is already doing).

1. He’s only 19 which is very young to be the “#1 sales dude” for any company. Unless he’s extremely well known in the industry (and it sounds like he’s not) he needs credibility so he should become obsessive with gaining product/industry knowledge. He says he’s doing that already but he should double down on those efforts. Spend every available minute pouring over product information and reading anything he can get his hands on. Most importantly, know how his product impacts companies. Don’t just learn the features…know the benefits and practice articulating those benefits. He’s a kid and people are going to see that when they meet him in person and hear it in his voice when they speak to him on the phone. The best way to overcome that is to know what he’s talking about. If he’s an expert and he can help people be more productive/effective/profitable, they’ll listen to what he has to say.
2. At this point in the game, he’s got nothing to base his “I know a better way of selling” ideas on but he can begin to change that. Boston is a major city and I’m sure there are some very active local tech networking groups. He should attend every tech function he can. Every tech networking event. Every local tech “awards” night. Every event where he can interact with people involved in the tech industry. These events will help him expand his contact base, which I’m sure he needs to do in the worst way, but it will also build his industry knowledge very quickly. He’ll find out who the industry leaders are and which companies/trends are hot. He’ll also pick up leads and/or hear of opportunities that he may have never known about.

With #1 and #2 above, he will able to speak with much more confidence and authority which will greatly increase the odds that his message will be heard, regardless of age. I agree with him that the more personalized approach is more effective than the “smile and dial” but without a solid base of reference within the industry, it’s going to be very tough to ever have a shot building the relationships that he wants.

George Penyak Adds:

I’ve got some thoughts/content below, Mike hit on a ton already, feel free to weave in as needed for the blog post:

First off, I love the young “hustler” mentality he seems to have!

He’s definitely doing the right thing by proactively, in his free time, becoming an SME in his field.  This will build more credibility with his customers/prospects, but also, his CEO.

To answer his question regarding a conflict with leadership on the sales process:

The Go To Market strategy almost always is a top down decision – there are likely long term strategies in place as to why that company goes to market the way they do (“smile and dial”, in person, through marketing, outsource, etc.).  For a start up, there are a number of factors that probably go into this decision, such as resources at hand – marketing dollars to spend, # of sales people the start up can afford, burn rate on current $ on hand, exit strategy….etc.

Another large factor on why/how a company goes to market is the complexity of the sale and product itself, if they are a tech company with new IP and strong patents – maybe a different approach is warranted, if they are an add on to existing software and have a massive potential market (geographically and market size) but little resources (like most start-ups), you’re almost forced to smile and dial.

Typically the quickest way to touch as many potential customers as possible is via phone and email, though less impact to the end prospect, you’re getting your message out to more people, faster.  Which makes sense for a tech start up that’s had weak results.

Considering his age and tenure – if he truly wants to build his own sales process, the best way to get support from his manager / CEO, is to master their process first – then slowly integrate in his own style in a collaborative way.  But a few things need to happen first:

1) He MUST becomes more of an SME in his field and industry, not impossible at his age, just takes more effort and work outside of normal hours.

2) Give 110% to the CEO’s / leaderships go to market strategy

Once that happens, if he’s still determined to change the sales process and approach:

– Build data around his solution – offer up coffee / lunch to customers he sold – get their feedback to build data on how the sales process was for them, why did they buy, what drove the decision, timing for them, etc.

– OFFER up to his leadership team to TRY a different approach/solution, backed by data and research he’s done, that will dive more sales and revenue for the company.  Anything that will drive more business AND is backed by good data and research, will be much better received by his leadership team.  Opposed to him just challenging their strategy because he’s “the number one sales dude.”  Wrong approach.

Unfortunately for him, based on his notes “But guys, I am only 19 and barley know what I am doing” he has a long ways to go before being able to challenge the leaderships strategy.  Patience, hard work, and more of an open mind, will go a long way for him.

Lastly, if he is still dragged down by the leaderships approach, “number one sales dudes” are typically in high demand by many companies 🙂

Jacquelyn Nicholson Suggests:

1) Results always trump issues – if you’re performing with excellence, generally your thoughts, opinions matter. Drive results so you have more of a voice. Sounds like you already are, but just making sure.

2) Best to approach this situation with the leader with statements that are questions and observation oriented that lead this person to where you want them to be. Generally if their reaction is very short-sighted, it is an emotional or reactionary approach, and you have to try and coax them out of their emotional reaction. Confrontation isn’t going to serve you well with the power differential here. Assuming the person is reasonable and open to ideas, you will be able to get somewhere if you ask great questions like “Have we thought about this…?” or “Have we considered…?” Statements combined with questions like, “I’ve observed this when we do that…what have you seen?” or “In my approach, I have seen this work well. What do you think about that? What are your thoughts?” Saying things like, “That’s an interesting approach, tell me more about why you think that.”

3) Don’t be the complainer – your boss needs you to support him/her and your job is to make their life easier at work. Instead, drive results and be thoughtful. If you drive success and are more of a person who is magically adding value and not always opening your mouth with negativity, this leader, if they have a brain and are curious, they will come to you and say, “Hey, I’m interested in your thoughts…”

4) Think of it like planting something…. like you would plant a garden – the seeds can be an idea, you water it a little and give it a little sun, then you stop – you shut up – i.e. no more water or sun for a bit – i.e. no more requests, complaints, asks. The opportunity will come up to discuss again and then you ask questions or give ideas – i.e. then you give it a little water and sun. Before you know it, boom you have a plant!

5) If this person is a jackass and completely not open to considering your thoughts and you’re successful and driving results for the company, start looking around for another job if you’re miserable. Don’t stay in a negative place for too long.

Kyle Gutzler Insists:

My advice is that I would listen to the CEO until you have a fact based reason not to. The CEO is working off a good deal of experience, and at 19 years old you still don’t know what works for you. Also, your “style” shouldn’t have much to do with your personal life. For example, in life you might do things that win you friends, which doesn’t always translate to business and help you win customers. Listen to the CEO and take his advice for your first experiment. The worst that happens is it doesn’t work for you, at which point you probably have a lot more leverage to try a new approach.

Scott Ingram Concludes:

Finally my own two cents. Do it your bosses way 110% like George Penyak suggests, and track your results. Likely: Dials, conversations, conversions, etc.  Then on your own time try the approach you think is going to work better, and again track the results. Be patient, you want to have a pretty significant data set. Over time you should have enough data to prove which approach works best AND you will have shown your value by going way above and beyond to build the case. Data and results are hard to ignore.