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“It’s about getting into the right mindset.” With Mitch Russo & Isobel Rimmer

I totally believe that EVERYONE can enjoy business development — from the geekiest software engineer to the most introverted specialist lawyer — it’s about getting into the right mindset, having access to a toolset and developing confidence through your skillset. As a part of my series about how to be great at closing sales without […]

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I totally believe that EVERYONE can enjoy business development — from the geekiest software engineer to the most introverted specialist lawyer — it’s about getting into the right mindset, having access to a toolset and developing confidence through your skillset.


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 Isobel Rimmer, Founder of Masterclass Training

Author, educator and business leader, Isobel believes that reframing selling to ‘helping people solve a problem’ allows us to unleash everyone’s potential to work in an authentic, natural way. On graduating she joined Digital Equipment on their fast track sales programme, before setting up Masterclass a global provider of training and coaching. She has 3 children (cost centers as she calls them) and lives for the day when they become profit centers and she THEIR cost center


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?

Like many graduates, I never considered a career in sales. Then I discovered that ‘selling’ was really just about being curious and I was incredibly lucky to join Digital Equipment (DEC) on their fast track programme and to learn so much. I went on to found Masterclass Training and for the last 25 years I’ve worked with many global clients (IBM, Citrix, Trend Micro, PricewaterhouseCoopers) designing and delivering development programs at every level from C suite to first time, frontline individuals. We now have over 70 trainers and coaches around the world.

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?

As a rookie sales engineer, I had a meeting with a senior VP of a large financial institution, a major decision maker and influencer and someone I thought I should impress.

As we walked down the corridor, coffees in hand, I asked him, ‘So how many people work here?’ Good, open question — or so I thought.

‘About half of them,’ he smiled back.

Did I feel silly! My epiphany moment came with the same VP about a month later and I was conscious this time about not asking dumb questions. We had forty-five minutes together and my questions were much better prepared and all about what he was trying to achieve with the business. Not once did I talk about what we could do or what products or services we had that might help — tempting though it was. At the end of the meeting, as we were wrapping up, he said, ‘Well, Isobel, that’s been really useful.’

Frankly, I felt a bit of a fraud. ‘But I don’t think I’ve really helped at all.’ I certainly hadn’t ‘sold’ anything or talked about what we could do.

‘Oh no, you have, it’s been really useful, you’ve helped my thinking — I’m much clearer on what we should do now.’

If you’re thinking — you missed a chance there, Isobel, don’t worry. He became one of our most loyal, high-spending customers, and a few months later signed off a $2 million deal.

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

My book, Natural Business Development was published a few weeks ago and is now a #1 best seller on Amazon. That has been an amazing journey. We are now delivering the training programme that supports it and, with Covid, doing that exclusively virtually. Many people said it just can’t be done with webinars and Zoom coaching. But the first cohorts have been fantastic –and we haven’t even finished the programme — it just goes to show how we can adapt and succeed if we are curious about trying new things.

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 first conscious experience of this was when, aged 18, I worked in a wine bar. It was my second Saturday night and the owners said, “Isobel, we’re going to leave you in charge tonight. You’ll be fine. If you have any worries — just call us.” They trusted me — indeed empowered me — to step up, take responsibility when I wasn’t convinced that I had the skills, knowledge or experience to do so. They, literally, gave me the key to lock up at the end of the night and believed in me at a time when I didn’t believe in myself. And, of course, it did go ok — I was never going to let anything go wrong on my shift! And I think they knew it. I am still incredibly grateful to them all these years later.

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

Almost my entire career has been in sales and I’ve always carried a quota — and still do. I love to help people develop their sales skills and for over 20 years have run sales and business development programs for thousands of people in product sales, consultancy and professional services. To see these people grow and thrive when they first thought they couldn’t ‘sell’ is hugely rewarding. But it’s also about helping seasoned salespeople become even better at what they do, too. Whether that’s presenting at conferences or in virtual ‘kick offs’ or preparing them for strategic bids and pitches. I’ve also worked with many bid teams — in one, my client secured a 10-year contract valued at over $1 billion. After 18 months of working on the bid, and the number of bidders reduced to three, they were told that only 3 people would be allowed to pitch to the Board. They would have 20 minutes to present and 20 minutes to answer questions. NO POWERPOINT SLIDES were allowed. My job was to make those 40 minutes the very best they could be.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

The last few months have been incredibly hard. We’re working differently, we’re living differently, we’re in unprecedented times. I think one of the most important things we can do is to connect with one another and to listen, without judgement or opinion, to their concerns. We don’t have to come up with a solution or a way forward, just really listen to understand their fears and worries and what else may lie behind them. Be there to support and show that you care. We will come through this.

My younger daughter is severely disabled — and for many years I went through life thinking, “What if…?” “What if they’d identified the problem sooner? What if she’d had antibiotics earlier? What if they hadn’t stopped my contractions…? And then, I had to come to terms with her situation. It wasn’t going to change but my view of it could. It was my choice and my choice alone. She still faces huge challenges, but I funnel my energy into making a difference, not thinking, “What if….”

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?

Two words: intellectual snobbery. Selling is still seen, by far too many people in far too many influential roles, as ‘something that you do if you can’t do something else.” And YET, nothing happens until someone sells something. All businesses depend on sales. All great companies succeed — or fail — because of revenue and sales. I’ve worked with lawyers who just want clients to buy from them because of their exceptional intellect and knowledge. Consultants who would rather have their fingernails pulled out than be considered ‘sellers’. We have to reframe what selling is — it’s helping other people solve a problem and want to buy from you — and show them how to do it in a way that is natural, authentic and honest. Simple.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, 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?

It’s the difference between being ‘curious’ and being ‘nosey’. One is genuine and engaging, the other is seen as pushy or inappropriate or for self-interest. If I am genuinely interested in my customers and prospects, genuinely interested in what they do, what they say and why they do what they do and say what they say, then a natural conclusion is that I will want to help them. The more I understand about them — I call it ‘what’s bleeping on their radar’ — and the more I want to help THEM succeed, the better. Yes, this may mean I need to make contact but if I am doing so because I believe that I may be able to help them, it’s out of a genuine desire to make a difference and, as we said before, help them solve a problem. If I’m trying to get something for myself, then most customers can see that a mile off — and that’s when it appears that we’re ‘pushy’.

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?

Over the years I’ve had Sales VPs ask me to help their teams ‘close better’, ‘sell better’ or ‘ask for the order’. And I understand their frustration when some of the team members can’t or don’t appear to want to ‘close’. But every time when we delve deeper, the issue is much further up the sales funnel or earlier in the sales cycle. They can’t close because they don’t fully understand the world of their customer. This phase, I call it ‘discover’, is at the heart of effective business development and selling. If we understand better what drives a buyer’s motivation or need — even when they don’t fully understand it themselves, because that’s always possible too — we build greater empathy and understanding. We are then far better able to present — or as I call it ‘share’ -what we can do to help them resolve the issue they have. So, the better we are at questioning and listening, really listening to understand not listening to unload our own ideas, thoughts or opinions, the better able we are able to position or pitch our offering.

I met the VP of Marketing of a major technology company. We started talking about her team and how they struggled to articulate their story and roadmap of products to analysts and technology leaders. I asked questions, she talked me through the issues. She was clearly frustrated and wanted results, quickly. I summarized back in a short email — she was a very busy person and didn’t want long complex proposals: “If I’ve understood you correctly you need them to do x, y, and z and therefore we should look at doing a, b and c.” It wasn’t a full proposal just clarification of what the problem was, what we could do to address it and indicative costs. I got the shortest email sales order ever, a one liner: “Spot on. When can you start?”

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?

My mother used to say, “Cast your bread upon the water and you’ll be surprised at what comes back.” I do believe you have to ‘give’ to ‘get’. Prospects need to know what you can do or offer before committing fully. In our world of training, development and coaching, this can be attending a free event or webinar, hearing a trainer talk live or read a copy of a book or article. Your best opportunities come from recommendation — so making sure that we stay close to our clients and support them so that they want to recommend us to others or to colleagues. This is easier if you consistently demonstrate the value or the return on investment that you delivered. The more you make your current customers look like heroes in their own organisations, the more they are likely to recommend you.

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’?

In the final stages of a ‘deal’, salespeople can be like athletes sprinting for the line. They’re nearly there, they can see themselves winning and they don’t want anything to get in their way. So, when an objection, barrier, or resistance comes up — whatever it is and however it manifests itself — the urge is to push it to one side and surge on regardless. But pause for a moment and consider what an objection or a stated resistance really is. Let’s take price — the seller thinks it’s a fair price, the buyers thinks it’s expensive; your product addresses all their issues, they’re not so sure. You think your team of consultants or lawyers can do this job easily, but the client isn’t convinced about their experience. In each case we have what I call, a ‘gap in understanding’. The seller sees it one way, the prospect another. There is a GAP in how we see things. Reframe ‘handling objections’ to understand what the gap is and looking to close it and life becomes easier.

To understand what lies behind an objection, we go back into the ‘discover’ phase. We overcome objections by asking questions and listening, not telling them why they’re wrong, or worse, dead wrong or trying to justify. Ask good questions and the customer may even address the objection themselves. Let’s take the issue of experience. We first show that we understand, we ‘get’ what their concerns are. “If I’ve understood you, you’re not sure about the experience of the team on this project.” In this short statement, I show them that I’ve heard them. I can then ask a very simple but powerful question such as, “Ok, so can I ask, what would you need to see, or what would you need to know about them, to be sure they have the experience you’re looking for?” This allow the prospect to reflect on what matters to them and tell me what they need, creating a shopping list of all the things that they want to see. We’ve gone a long way to closing that gap.

‘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.

Traditional sales training often takes the view that closing is all about the salesperson being ‘in control’. Flip that around. Give the control to the customer (they always had it anyway, just sellers like to think they have it too!) and make it easy for them to want to buy from you. Help them to make it their decision, their idea and help them to see that working with you will bring results for them.

I was introduced to a Senior Partner in a large consulting firm. First, we had an initial exploratory meeting for me to understand his world. Secondly, we walked through a ‘discussion document’ over a conference call that framed how we could approach the project — not in great detail, more how it would work and what it could look like. Third, I asked him how he would measure the success of the programme and suggested that he think about what metrics would matter most to him and suggested we discuss those when we next spoke I believe a client should be able to measure the impact or the ROI (return on investment) they get. He then created a list of ‘metrics’ that would be good for him, his team and that he could measure. These included new opportunities for his consultants to bid, new opportunities in existing clients and improvements in bid: win ratios (they spent a lot of time preparing bids but their hit rate was poor). Some were less tangible — he wanted his consultants to enjoy the idea of business development too and devote more time to it. We talked about what these could look like and the value they would bring in the future. By now he was in control of what he could see happening. So, my fourth point is always help your client to see what success working with YOU will look like. These were HIS numbers, HIS business opportunities, HIS timescales. He wanted results and he wanted them now. He could visualize what success could look like and the difference it would make to his life and his position in the business. He was in control and he wanted to get started. He closed the deal.

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?

Get commitment to joint action early in the process and in the relationship. It’s always better to assess how serious someone is about wanting to work with you before you invest a lot of your precious time, money and resources in chasing them. When I train this, I start by asking one of the delegates if they like me. Being polite they usually say yes (whether they like me or not!). After all, it’s easy enough to agree on that one and move swiftly on. “That’s great, I say, would you like to marry me?” at which point they usually fall off their chair or at least fall about laughing. But the point is — they’re not ready for that level of commitment. We’ve only just met and I’m already talking about marriage. But… if we’ve been talking for a while and I want this relationship to go somewhere, it’s time to start asking for some kind of commitment to something that we’ll do together. If they ask for a proposal — I ask if we can arrange to get together or have a conference call to talk it through. If they won’t give me 15 minutes for that, how serious are they about working with me? We have to give some things away as sellers in order to progress an opportunity but if there’s nothing coming back, no reciprocal commitment, find out early in the process.

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?

I believe that if you’ve done your best at every phase: you’ve connected with the other person(s); you’ve discovered what’s going on in their world and what matters to them right now; you’re genuinely interested in what they’re trying to do and the challenges they face; you’ve shared your ideas, products or services and demonstrated that you have the experience and potential to support them; you’ve looked at ways you can collaborate and work together getting commitment to some course of action- then, you can ‘close’ using any medium. Ask them early in the sales cycle what their preference is. Some love to ‘jump on a conference call’, others prefer to meet in person — be guided by them. Remember, it’s not about you, it’s about them.

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. 🙂

You’re very kind to suggest that I’m a person of enormous influence! I’m just doing my bit to help people overcome the fears, worries and concerns they have about selling. I totally believe that EVERYONE can enjoy business development — from the geekiest software engineer to the most introverted specialist lawyer — it’s about getting into the right mindset, having access to a toolset and developing confidence through your skillset. It’s also about reframing — showing them that business development and ‘selling’ (eek!) is all about helping customers solve a problem and making them want to work with you. It’s about unleashing the potential of everyone who, directly or indirectly, has a connection with customers to spot opportunities, develop new business and grow revenue.

Thank you for taking the time to talk to me today, it’s been a real pleasure.

How can our readers follow you online?

Isobel Rimmer: Linkedin https://www.linkedin.com/in/isobel-rimmer-0a23541/

And all my ideas are in my book — Natural Business Development by Isobel Rimmer)

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

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