Omar Dousheh: “Don’t sell past the close”

Don’t sell past the close. As we get more seasoned, our ability to recognize when we have secured a sale becomes more prominent. However, I’ve noticed more novice sales reps talk past the sale. Some have even talked themselves out of it. Having the awareness to know when your job is done and securing the […]

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Don’t sell past the close. As we get more seasoned, our ability to recognize when we have secured a sale becomes more prominent. However, I’ve noticed more novice sales reps talk past the sale. Some have even talked themselves out of it. Having the awareness to know when your job is done and securing the customer might sound basic for some, but is a challenge for others.


As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Omar Dousheh.

Omar is a B2B Sales Professional with 10+ years of experience serving a variety of industries. His passions include understanding top of funnel buyer behavior, how sellers can intersect more effectively with their target buyers and sales process optimization.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I’ve been selling in one way or another for as long as I can remember. When I was a child, I would go door to door and ask my neighbors to clean their snow or rake their leaves for a small fee — I was always looking for different ways to make a buck. Once I graduated from University, I received an opportunity to work at a management consulting firm as a business development representative. I had overheard one of my colleagues mention the size of the commission checks being earned by other representatives — this made an impression on me and I thought that there could potentially be a career in this for myself.

In the early days, the allure of big commission checks pulled me towards sales, but I quickly learned that you burn out if you don’t have a greater purpose. What keeps me in the profession is learning, building and my professional development. I imagine myself as a stock; the more I can learn and grow, the more my stock price goes up, and if i’m not developing my skill set and increasing my value my stock price goes down.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Roughly 5 years ago I was interviewing for a new sales role and I was at the finish line with a large and well established Canadian technology company. I had completed 5 interviews and as part of their final stages they requested I meet with their CEO. I was at the tail end of their process and we were discussing the terms of their offer. That’s when a recruiter reached out to me about an opportunity with a small startup. I told her she was too late because I was expecting an offer in the coming days, but she pushed back and explained that the company in question could move quickly because they were small and nimble.

I continued to pass on her request, but she was very insistent and eventually I agreed to a few discussions with their leadership team, which led to a deep appreciation for the organization and product. I was hired as employee number 30 and we grew to over 150 employees over the course of 4 years. The company went on to become one of Canada’s fastest growing startups and was eventually acquired.

The best experiences I’ve had are the ones that challenge and push me. If I could share one lesson, I would advocate to capitalize on opportunities that push you out of your comfort zone. The earlier you are in your career, the more risks you can take. As we get older and have more responsibilities, the less risk we can take on, but in your early days make it your intention to get uncomfortable.

Are you working on any exciting new projects now? How do you think that will help people?

I’m dedicating some of my personal time towards creating content on Linkedin. I’ve taken a real interest in writing about sales as a performance based profession. If we think about it, sales and sports share a number of common characteristics like resilience, goal setting and focus (to name but a few). I think it’s a unique angle that can potentially demystify top performers and enable us to eventually replicate results.

By simply writing about these topics and starting a dialogue we can pique the interest of those who might be interested in a sales career. In addition, we can educate those who are in the profession and looking for ways to elevate their performance.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My high school football coach changed the trajectory of my life. I never cared much about school and it showed. I was the classic class clown with zero goals or aspirations. The one thing that I did take seriously was football, it brought me purpose and meaning. The high school I was attending didn’t have a team and so I transferred to a school in a different city so I could play.

My high school football coach (Rick Maloney) was also the school’s guidance counselor and he made an effort to spend time getting to know me. He took an empathetic tone, but was also stern when he knew I was trying to BS him. He pushed me when no one else did (which showed that he cared) and challenged me to apply myself in academics in order to pursue football at the next level. Playing football at University is something that I never considered doing, it was a thought that never entered my mind seriously. I’m the youngest of seven kids, and no one in my family had attended University, so I never thought to myself that I can or I should.

In those final years of high school, I pushed myself on the field and in the classroom. I finished as an All-Star in my league, and our team went on to compete in two finals championships. I did my best in the classroom, but I was unsure if it was enough. I applied to three schools, and got rejected by two. It was down to one school and I was over the moon when I received my letter of acceptance from Wilfrid Laurier University.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

I wouldn’t consider myself an “authority” as such, but I’ve been in the industry for over a decade and I’ve learned a few things along the way. I’m fortunate to have experienced being both a top performer and an average one. To have witnessed high performing teams that elevate the profession and toxic cultures that bring it down. All experiences are a blessing that I am grateful to have gone through. They add to my lessons learned and content I can share with others who might need to hear it.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

I’m not sure exactly why a skill as important as sales is totally ignored. Sales touches almost every facet of our lives. Ordinary tasks like trying to convince a child to eat their vegetables or negotiating the price on an item you want to buy all involve sales skills to some extent. Sales is literally all around us if we look for it. We have simply gone numb to it in our day-to-day lives.

Generally speaking, our education system does a poor job of preparing our youth for adulthood. The gap that exists between the education we receive and how it’s applied is grand canyon-esque. On a brighter note, the Ontario Government recently announced that math classes will include topics related to financial literacy. Practical topics like getting a loan and paying debt are going to be taught more frequently. Many people are excited about this new milestone. Maybe one day they will incorporate sales into the curriculum too.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

One of my favorite sales books is called The Challenger Sale. The authors conducted extensive research in the area of B2B sales with the intent of identifying the characteristics associated with top performing sales professionals that they call “Challengers”. There are a number of traits that characterize a Challenger; for example, knowing when to teach and take control of the buyer journey. The authors also find that top performers know when and how to apply pressure in the sales cycle — the appropriate amount of pressure is required in all sales cycles, but knowing how and when to apply the pressure can be the tricky part for some sales professionals.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

My strongest skill is prospecting. I have a high regard for sales professionals that can generate new business through top of funnel activities. It is also something I am passionate about. The skill set associated with prospecting is of high value to any organization. It also gets me really excited when you can successfully take a prospect from a cold call to an introductory conversation. It’s the most challenging step in the stages mentioned above and very few people can do it effectively.

When I was selling into the Oil & Gas industry I closed a transformational deal with a leader in the space. One of the first things I did was reach out to our marketing department and collaborate on an interview with the customer. We published the case study and I leveraged the collateral to educate the market about the work we were doing with their peers. Such social proof can be used to guide prospects along their journey and facilitate the change from “problem unaware” to “problem aware”. Marketing materials are scalable, which bestows a high value on them. In this particular example I was able to leverage the content to prospect more effectively, generating more pipeline and eventually closing business.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

The idea of prospecting is basic, executing it is hard and scaling it effectively across a sales organization is extremely challenging. I’m a firm believer that your existing customers can pave a path forward for your lead generation efforts. In order to generate good, qualified leads, you have to know who your ideal customer is. The more time you spend with your customers conducting interviews and learning about their priorities, reasons for change, and business outcomes they drive towards, the better prepared you are to identify your Ideal Customer Profile (ICP) and guide their buying cycle.

Once you’ve earned the right to have a conversation with your prospects, you can pivot into question asking mode and aim to identify if they are a good fit. The last thing you want to do is get a false positive and allocate business resources to a prospect who has a low propensity of becoming a customer.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

When you’ve had enough conversations with your customers, patterns in their objections will begin to show. You might even be able to map out your sales process and predict which objections will surface depending on the stage.

After a while there shouldn’t be any surprises. You will have all possible objections documented, with prescriptive methods to alleviate those points of friction. One of the root causes of poor objection handling is a weak pipeline. When reps don’t have enough opportunities to get to their number, they start qualifying when they really should be dis-qualifying — and that’s when things can get sticky.

My recommendations are two-fold: First, document the objections you are receiving and have a plan in place to solve them. Second, maintain steady pipeline generation activities and ensure you have enough opportunities to work should you need to disqualify prospects based on the objections they surface.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

Some say that ‘closing’ happens in the final stages of a sale, I believe it happens throughout. Below are 5 themes that can help us be more effective closers without being perceived as pushy:

Spend time understanding your Ideal ICP. Learn about their priorities and the language that they use to describe their challenges. Sometimes the best technology doesn’t win evaluations, instead it’s the vendor that understands the customer’s problem best.

In my early days selling Advertising Technology, I suffered from imposter syndrome. I was a couple of years out of school and unsure how I could possibly become a trusted advisor to leaders that have been in their industry for decades.

What value could I possibly bring? However, over time I was able to develop product expertise and serve a need that surfaced through conversations with my customers. The need was located at the intersection of the customer’s business problem and our product functionality. That’s the sweet spot. Who better to talk to the customer about how your product can solve their problems than you!

Your discovery determines your success. Most reps try to fit a square peg into a round hole. They very seldom ask the upfront questions required to disqualify an opportunity. We are stewards of company resources and part of our role is to Identify where best to allocate those resources. Ask the questions you might not like the answers to, as early as you can. By making an effort to get to ‘no’, when you get a yes it will be much more valuable.

Solve for outcomes, don’t demo features. Generic demonstrations that highlight product features are table stakes. Our job is to understand how our products impact the customers’ business. Products become solutions when we marry them to customer pains. Nothing says ‘closing’ like delivering a demo that wedges your competition out of an evaluation.

Always have the next steps secured. In some instances the next steps can’t be agreed upon or scheduled. I do understand that. However, at the very least set up a 15 minute ‘follow-up’ call at the end of your meeting to determine how both parties should proceed. The last thing you want to be doing is playing chase and sending those “touching base emails”. No one wants to have their base touched!

Don’t sell past the close. As we get more seasoned, our ability to recognize when we have secured a sale becomes more prominent. However, I’ve noticed more novice sales reps talk past the sale. Some have even talked themselves out of it. Having the awareness to know when your job is done and securing the customer might sound basic for some, but is a challenge for others.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Customer interest doesn’t necessarily translate into customer preparedness to buy. Unfortunately, many of the marketing tactics leveraged to convert a lead into a Sales Qualified Lead (SQL) do not necessarily mean that the prospect is at a point in his or her journey to make a purchase. For example, if a customer downloads a piece of content, they may then get spammed with phone calls and emails even though they are not ready to speak with sales. So gated content that’s gated for the wrong reasons can be a part of the problem.

When all prospects get treated the same (blunt sales rep engagement), you get a sales force intersecting with prospects at inappropriate stages of their buying journey and this is why the tactics used by reps are perceived as “pushy” or “overeager”. Thus part of the problem is expecting sales to deliver unreasonable results with prospects who are not at the appropriate stages of their buying cycle.

Finally, sales reps need to spend their time where it matters most, with the prospects that fit into their ICP. My recommendation to business leaders is to know your ICP inside out.The research and documentation that you gather can help build out your messaging and qualification framework.

Qualify out of the wrong opportunities and into the right ones.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

Text is a no go area for me, unless my customer gives me permission or prefers to communicate in that channel. Ultimately your customers decide which channels are best. For example, some customers can be in back to back meetings from 9–5, so reserving call blocks in the mornings provides a better chance of connecting.

Buyer behavior is intricate and differs on a case by case basis, but if I had to choose which methods are best, I would take a multi-pronged approach. Too much debate exists around phones being dead, sending emails versus inmails, when to use video etc. The list goes on. The best approach is one that incorporates all channels and gets executed.

In my early days, I didn’t have much of a strategy when prospecting. Every once in a while I would taste success, but I didn’t have a set process to produce my desired outcomes. Being exposed to veteran top performers changed my perception of the sales craft. I noticed that the best sales reps had a process in place for engaging with their customers. They could clearly articulate how they would start the conversation, their tone, the direction they would take it and why. I followed suit and began documenting my process too. As I started getting more wins, I was able to identify the “how” and share those learnings with my peers. That year I inherited a team on track to miss quota. I was able to share key learnings that aided in overall sales process optimization and support the team towards a successful year end finish.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could inspire a movement, it would be to motivate the next generation of professionals to be intentional about a career in sales. Most of us in sales end up in the profession by accident. A stroke of luck for some and a mistake for others. At the beginning of this interview we discussed the gap that exists between the education our youth receive and their level of preparedness for the real world. I believe if we spend our resources preparing our youth more efficiently with skills that are in demand, such as sales skills, we can begin to see a more intentional generation of sellers.

How can our readers follow you online?

Please connect with or follow me on LI https://www.linkedin.com/in/omar-dousheh-82037253/

Thank you for the interview. We wish you only continued success!

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