Connie Smith, Sales Consultant and Trainer

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Connie is one of the most marvellous networkers I have ever met, which is clear from her calm composure and evident emotional intelligence from the moment you meet her. Her willingness to give without the requirement of return is a credit to her character.

Connie and has crucially helped me to source the Head of Sales for my own business – who is in her own right a wonderful person and top performer. I’m grateful for her contribution for the book.

You can read Connie’s full biography here 


Jamie: Connie, what have you found most fulfilling in your career thus far?

Connie: I think what’s exciting about sales is that it’s not restricted to any industry or sector. I think that’s really important to know. What I love about being in sales is that I can work in education and property, technology, and then eventually I’ve managed to find my niche which is within development, so working with social enterprises and organisations in Africa. Regardless of whether you’re working in America, the UK, or Africa, it’s a transferable skill, and so I’ve been able to travel with my work.

Jamie: Have you found that challenging, switching industries?

Connie: Certain fundamental principles apply to all sales, regardless of the sector or the product. Although the product has varied,I have always believed in its value. I think this is a very crucial part of selling – believing in the product you sell. There are different kinds of sales, and each one requires a different kind of conversation, B2B, B2C, FMCG. I would say that the biggest challenge was graduating from selling a product in a 20-minute conversation to managing stakeholders over two- to six-months to close huge consulting deals worth hundreds of thousands. I think getting great at the complex sales is what I have found most rewarding, but I must say that there is something nice about having a quick sale after 20-minutes. There’s a great feeling about making that sale that never gets old.

Jamie: Which do you prefer? 

Connie: I would say definitely complex selling and the reward that you get when you’re able to understand the psychology behind why people buy and are responsible for guiding decision-makers through a smart buying process.

Getting really great at complex selling is knowing when to listen, the right questions to ask questions, and the right time to tell the right story, as well as speaking to the right person at the right place, and at the right time.

I find that really rewarding- helping people to make the best decision based on all of the information.

Jamie: Do you think that complex sales is usually better compensated?

Connie: I would say in the majority of cases, yes. It becomes complex when you’re dealing with larger amounts of money or selling bigger products or services, but that’s not to say that someone couldn’t sell many of the smaller products and hit the same targets. From my experience, technology and SaaS sales is where a lot of the money can be made, as the value and margins are big. However, I prefer selling consultancy services despite the lower profits in human resources.

Jamie: What sort of characteristics would you say a person needs to have above and beyond a simple sale to be able to get into complex selling?

Connie: The first skill would be to be an exceptional listener. I think that is the number one skill. You are removing the pitching element in exchange, and you are trying to deeply understand what that client or organisations’ challenges or problems are. It’s moving from a consultative sale where you just listen for queues to answer with a pitch, to taking it a bit further and really building those relationships where that person understands that you’re really listening to them. Listening to understand and not jumping in.

I would say another one would be being able to manage your time really effectively and knowing how to manage stakeholders. With complex selling, you’re typically speaking to a wide variety of people in different departments; so you’ve got buyers who are very difficult to sell to, you’ve got executive directors, CEOs, internal sponsors, as well so people who are going to be using your product and can influence the decision-makers. It’s understanding how all of those people play a role in the sale, knowing how to build relationships with each person, and knowing how much time to spend doing so.

Jamie: Do you think there is a personality type that is better suited to sales?


I think people attracted to sales tend to be very self-motivated and driven. Having worked with thousands of people in sales, I find that when they take personality tests, typically the most successful tend to be those that want to be leaders; they’ve got to be confident and quite independent.

It often means that within sales teams there are a lot of egos. Coachability is also one of the key things that makes somebody good at sales – a person constantly willing to learn, adapt, and be flexible. 

Jamie: Would you also recommend any salesperson or any personality type go into sales consultancy?

Connie: I found myself in a sales consultancy role almost by mistake, but I have really enjoyed teaching and coaching for over five years, everyone from executive leaders and directors to farmers in villages in Africa. I believe to be a credible sales consultant, you need to continue to be a salesperson in some capacity to keep your skills sharp and knowledge current. For example, as an independent sales consultant, I end up selling my services as well as delivering them.

I would definitely recommend sales consultancy, but not to anyone, I would say sales consultancy suits people who are really flexible and want to keep learning. The thing about consultancy is that you’ve got to be willing to learn about lots of different sectors, as you are not specifically working with the same people or organisations. So, you’ve got to be adaptable, flexible, and ready to change what you’re doing, think outside the box and be open to learning about different cultures and contexts.

Jamie: So there’s not a lot of structure in most sales consultancy jobs?

Connie: There are frameworks in place with most consultancies, but you have to stay open to clients’ independent needs, as each is at a different stage with different challenges. As a consultant, you shouldn’t require constant hand-holding, even when there’s not a lot of structure. A risky part of being a consultant can be that you end up in a silo, working alone. If you’re working independently, and not as part of a group or team, it’s about ensuring that your skills stay acute, that you’re constantly learning and developing, getting a second opinion because if you’re on your own, you can get stuck in your own methodologies and practices and not be open to seeing where the opportunities are. That limits your capacity to support your clients and grow.

Jamie: What do you think is your personal biggest strength as a salesperson?

Connie: I think my personal biggest strength as a salesperson is allowing people to feel very comfortable with me. I think I find it very easy to connect with people and for them to trust me, which is the first hurdle in the sales process. Networking is definitely a big strength of mine, and meeting people, making first impressions and being memorable.

Jamie: How did you learn to network or what techniques do you use?

Connie: Part of it is a natural skill, growing up in multiple countries and cultures. I had a diverse upbringing, born in Africa, moved to Scotland; polar opposites, and having experience of different backgrounds from very poor to extremely wealthy. It doesn’t matter whom I’m speaking to; I can somehow relate or adapt. For me, it’s a very easy thing to do. I feel comfortable doing it, and it’s very natural. However, I know many people struggle with it.

I was thrown into the deep end networking professionally and learned by practising. I guess if you don’t have it, you don’t have it. If you cannot make people feel comfortable because you are either socially awkward or cannot listen or to empathise with people, that’s difficult, but by practising, you learn how to become a better listener, connect the dots, empathise with people, and make them feel comfortable.

Jamie: What difference has being a good networker made on your career?

Connie: I am seen as and get used as a resource more often.

Being a good networker means that I definitely earned more money because of the people that I’ve been able to get in front of. It opens up a lot of sales opportunities and employment opportunities where a company will put me forward because of the opportunities I can open up for them.

I also get approached at networking events by people wanting to hire me.

Jamie: What are the biggest challenges you have currently to winning business?

Connie: I am selling sales consultancy services. It is not a tangible product. It definitely falls into the complex sale category. It is selling an idea; not an actual product, so you have got to be really good at telling stories. You have to give examples of how you have worked with other people and use data. What I think is really challenging at the moment is making sure I am getting in front of the right people and not wasting my time. As a sales consultant, you want to make sure that the people you are speaking to have the same attitude about sales as you. There is no point in me trying to work with an organisation where they mistreat their salespeople. I am trying to help people to be more mindful and purposeful about the way they sell and can only achieve this if the leadership has the right attitude towards the change process and the wellbeing of their people.

Prospecting for the right client and getting in front of the right people. Personally, I work in the impact space, so I find it challenging finding people and companies that can afford to work with me. Once I have done that, everything else falls into place, as long as you follow all the stages of the sales process. The biggest hurdle is making sure you don’t fall into the trap of sending out proposals and then chasing them up. I have corrected this from years of selling badly… “Just checking in to see if you have read the proposal,” and you just chase up these proposals again and again.

Now I never work on a proposal independently, but build them with the client in real-time; a collaborative proposal where they take ownership, and it makes the sale more certain and quicker.

We build it together on a video call, sharing a screen without sending it through to the first. Even the final version is reviewed over a call. I make sure there is no situation where I send a proposal without running it through with the decision-makers. It slows down the sales process at first, but then it speeds it up at the end.

Jamie: What is your favourite thing to teach people about sales?

Connie: I’m more excited about the context than the content. What I mean is that my favourite part of teaching is when I can do a live example, either including the person or people I am training or with a co-trainer so they can watch and have an experiencethrough role-playing. Whether it is showing them how to work territory, whether it is using names or stories, or whatever it is. I know I enjoy teaching softer skills, more than how to use your CRM. I really enjoy teaching people about the interaction between people, being able to role play, coach, and showing them versus just telling them.

Jamie: A lot of people would find role plays uncomfortable or difficult. How do you help people get over that?

Connie: If you are training or coaching your salespeople before they go out to do their job, then role-playing is absolutely critical. It allows them to make the mistakes, to feel all of that uncomfortable awkwardness that you do feel when trying something for the first time. It helps to just get it out of the way in a safe environment, then in the real scenario, it feels more like something they have practised. When someone is uncomfortable, as the trainer, I take the tougher role – the salesperson – initially to show them how it is done and take the pressure off.

The second part of coaching somebody really well is you then ask them to do it, but you do not ask them to do everything from beginning to end, you break things down into small segments. They can’t get it all right at once. You are not asking them to do a role play for hours and hours. It is just maybe 10 minutes of one particular very specific thing. You do it first, show them and ask them, what did they notice you do? What do they notice you say? What did they hear or see? You get them to download, digest and tell you, so it is coming from them.

Then they practice it, after which you give them feedback. You have to show them what they have done really well, and give them only one thing to work on and only ever one thing. If they try and change lots of different things, they will end up stopping doing all the things that they are actually doing well.

Give them three things they did well and then just one thing to work on. It is a different approach, and I found that to be way more successful than the “shit sandwich.” If they are really struggling, you show them again, but the idea is that the more often they can see it being done and the more often they can practice it, the more comfortable they will be in the real scenario.

Jamie: You worked across a range of industries. If you were a young aspiring salesperson, what industry would you go get into or try and get into?

Connie: Do they want to earn a lot of money? Do they want to be in an aggressively competitive environment, or do they want to be in a relaxed environment? Because sales environments are very diverse, and sales cultures within organisations can vary. I would ask the person firstly, what would their interest be? What is their priority? I would figure out what kind of person they are; what do they really want from the job? Depending on the answers that they gave me, I would be able to make a recommendation from that. When I was younger, I would have wanted to work with a big corporation, but now I prefer working with start-ups and social impact organisations. My advice is to g,et into something that they are interested in. Nothing worse than trying to sell something because you think you are going to make a lot of money, but you really do not care about the product or service.

Jamie: Let’s say you wanted to get into sales consultancy. How do you do that?

Connie: Firstly, do the time selling. I did 12 years of sales first, to get really good at selling. This helps as you then have stories, examples and experience to share with clients. You need to love sales, as this also translates to the clients and the people you coach. If you want to get into sales consulting, my advice is to read all of the books and understand the science behind selling. There are loads of sales journals, there are lots of podcasts and blogs, so making sales your life and being really interested in it, would be a great start. There are plenty of consultancies out there that will work with good younger salespeople. They do not always have to have as many years of experience but just that ability to be coachable and a good trainer. Never get into sales consulting if you don’t love or aren’t good at sales.

Jamie: What elements of culture have you seen in the organisations you work with that make for a great sales culture?

Connie: It might sound a bit mad, but one where people are not targeted. Where the salespeople are supported by their manager to help them align their personal aims with the company’s financial goals. I appreciate a culture where people are supported on the inputs and activities versus just the output and results—an environment where managers manage their team by coaching them ontheir skill sets, the competence.

Too often we hear “How many deals do you have? When are they going to close? How much are they worth?” which creates a culture of pressure. Instead, you should hear “Where can I help you, with what you are doing at the moment? Where are you struggling? Let us go through each of your deals. Where are they now? What stages have you been through? What stages have they missed? What stage are you going to next?”.

Jamie: What advice generally would you give to aspiring salespeople?

Connie: There are ups and downs in every role and every single sales job. If it was easy, everyone would do it. It is extremely hard. The biggest thing that you really need to focus on is your attitude. If you mentally check out of your sales job, you are not going to sell what you want to sell. So how you feel about your product, how you feel about your company, your colleagues, and your clients, or what you are selling is extremely important. Your success is tied in with how you feel about your opportunity, possibility, responsibilities, and creativity.

You are doing yourself an injustice when you catch yourself bitching about colleagues or complaining about your commission or thinking that the product is not right, and you will not sell effectively. The first thing is to look after your attitude before anything else.

I would also advise every salesperson to try working in different industries, different environments and seeing what you like and where you’re the best fit. Then you can specialise. If you decide to set up your own business, sales is a very transferable and a crucial skill, one that many start-up businesses lack.

Jamie: What do you feel is the role of sales in a start-up?

Connie: When I speak to a lot of start-ups, and this is across the board, and across sectors, founders will typically have a strong tech or finance background or what you call “business background” but they do not have sales skills or experience. In fact, people tiptoe around the word sales, and they call it “marketing.” Funding gets invested into operations, infrastructure, tools and leaving sales and building sales teams as an afterthought with less budget. Many people have this bizarre mindset that their product or service is going to sell itself, but they learn the hard way.

Even if there is a strong need for the product or service, it never ever sells itself, and you will only get the low hanging fruit at first before that all dries up. You can get early adopters, but once you have got those, then the market really changes and then you have to sell to the rest of the people.

It is much harder, and it requires actual skills. Often sales teams, along with HR, are the last to be invested in. Money is not spent there, and people often do not see it as an investment, despite it being the way the business generates revenue.

It’s a really strange phenomenon. I often have people come to me at a stage when their business is in trouble, and they need to grow their results exponentially! You cannot blame start-ups as they often have little capital. They do not always know what best practices are, they are trying to save money, so they will take things for free, which are not always the best. You find people doing multiple roles that they’re unqualified or unskilled for, but they eventually and hopefully get enough money that they can invest in developing skills, resources and the capacity building that they need.

Jamie: In your career, specifically, if you had it again, what would you do differently?

Connie: I think back on my sales career, and I realise I had some really good managers, but also some awful managers. Some were poor at management, aggressive or really manipulative and got me to sell for all the wrong reasons and therefore, at first, I was selling pretty poorly. I was selling really compulsively, really aggressively because

as a salesperson you are only ever performing at a state or level that your manager is. If they are harassing you for numbers, if they are in a survival state, that is exactly where the people they manage are going to be. If they have checked out mentally, then their team will do the same.

If you are furiously running after numbers, making mistakes, then that is what leads to burnout. My advice to my younger self who was in those unhealthy management relationships would be to “get out now, just get another job, because the reality is that everyone needs salespeople and there are loads of great sales jobs with great people and cultures.”

I would say to people, never feel like you are trapped in a sales job either because you have outstanding commission waiting for you or because you are being given false promises of pay increases or bonuses, that tends to happen a lot in sales. The way that businesses set up incentives and compensations are designed to retain people, and the salespeople are not always protected. I think as a salesperson you have got to protect yourself. Get out of terrible situations, cut your losses, and move to a different company for the following reasons:

(1) If you are not being compensated or treated correctly,

(2) If there is no progression where you are, and

(3) If you are not being developed.

Jamie: Can you tell me about a specific time where you did not make a sale, but you learned a lot from it?

Connie: Recently, I was working on a deal for a very long time. From meeting the first person at a conference in Kenya, building a relationship with this sponsor, to then getting introduced to the sales director, who I believed was the decision-maker.

I spoke with him for a good three months putting together this incredible proposal which detailed over 18 problems that the business had, that he just could not fix, and could not do so. We also had the business case, and they were losing about half a million per year of potential sales. We found a solution where we would come in do a light discovery call, train their team, help them with various tools like their CRM and then have a consultant remotely embedded. He was really excited to go to the next step. That was when I found out that he was not the ultimate decision-maker, and we needed to take it to the founder, who would then take it to the Board.

I realised that it is so crucial to find out right at the beginning of every sale who makes the decisions and not be scared to ask, rather than make assumptions. The other thing is to not be scared to speak to the person who is causing the problems in the business. It is really important to understand their side of the story too.

At this point, I wasn’t being granted access to the board, and the founder had not bought in. When the proposal was shown to the board another three months later, they said “no.” I wasted a lot of time, and I felt extremely disheartened as I had formed relationships with the sales leadership and wanted to help an organisation which was delivering impactful products. I wanted to put myself in their situation and wanted to help them solve their problems.  Being an empathetic salesperson is a double-edgedsword. The lesson that I took from that is not to waste my time with the wrong people, not to build relationships where they are not leading to results and reminding myself that, although I love my job and it is great, and I am helping people, it is a sale and therefore I need to be as efficient about my time as possible.

Jamie: Could you tell me about a time when you made a sale, and it really shows off all the things which you have learned and developed throughout your career?

Connie: Yes, a Fintech organisation in West Africa. They are a big and competent corporation. They approached us saying “these are the problems that we have and we need this specific support from you”. What I think I did really well was to slow them down. They wanted to get a consulting engagement that month, which would have been too compulsive. I slowed them down in the buying process, which ended up taking four months.

Most people would ask, “Why did you do that?” when they were ready to buy. The reality is if they had bought and we had delivered what they asked for, they would have spent less but it would not have solved their actual problems.

Instead, the contract value was for much more, and they didn’t choke on the price tag, because they knew the full extent of the scope of work required to solve their problems.




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