It’s fitting that this project should come full-circle, and the first interviewee should also be the last. Theo has been a huge supporter of this project, and sat down with me three separate times to share his exceptional career journey and what he’s learned so far.

This interview was conducted when Theo was a leading sales trainer at Oracle, a position he now holds at Google. He challenges the interviewer with great technique below!

You can read Theo’s full biography here

Jamie: Theo, when we look at the part of your career-related to sales performance training, what have you found most fulfilling?
Theo: We had a leadership summit in Dubai last week with all of our organisation’s Directors, and something that we agreed on was that we change lives. We change outcomes for people, and e solve very difficult, very frustrating, and challenging market problems.

Jamie: What have you found is the biggest difference between internal and external sales roles?
Theo: I am an internal cost centre; our internal selling is to get bums on seats in training – onboarding and continuous learning. That is a very different sale process compared to an external sale; there’s no real cost to all stakeholders in that we don’t charge them for training. An external sale would be very different if I was doing exactly the same business; there’d be a material cost, and a different decision-making criterion and process.

Jamie: How do you position the value?
Theo: We definitely have to sell in a consultative style. It involves problem-solving; like the doctor with their toolkit, the sales trainer or sales performance leader has a solutions suite. We approach it the same way as we would an external sale; discovery and trying to find out about the business; How do they measure it? How are they being measured? What are their perceived challenges at the moment? What are the ideal outcomes? What are their perceived solutions to get there and how do we add value, perhaps showing them that they don’t know what they don’t know? What else is out there? What is our capability, and what’s in our wheelhouse?

Jamie: How do you drive urgency in that role when people could just as easily postpone the sales training?
Theo: We have help from the organization. We have a system of badging where the procedure can help the qualifications of each rep. They have to work towards becoming badged according to their role. If the Senior Vice President or Vice President buys in, this will help his people buy-in. The senior leadership will mandate it down to the directors and the line managers who ultimately will get urgency from above. It’s all about who you’re talking to at which level to drive the urgency. But you’re right, if it’s not a senior directive, then it’s hard to get people to value something that seems free,
Compared to our direct competition, we may have the largest sales training business, compared to a lot of companies that will outsource everything. They only have external vendors coming in to do one-off trainings here and there. Our organization is certainly miles ahead of what else seems to be out there on the market.

Jamie: What material benefit would you say if you get this result?
Theo:

I love this question that managers sometimes have, “Well, what if I invest in training and they leave?” The other question to that is, “Well, what if you don’t invest in them and they stay? When you go to training, you’re really sharpening the sword.

You’re learning to ask better questions. You are learning to prospect better. You’re learning to discover better all the way through to handle objections, closing, pitching, and asking for referrals. I think that compounds over time because as people get better from training, they also teach their peers on the ground, in the trenches, and in the field. It’s changing culture. That is one of the hardest things to address in any organization, especially a large one.

Jamie: Why did you go into performance coaching and training?
Theo: I actually always dreamt of being a teacher – making all the money in finance and real estate and then semi-retiring into teaching, and somehow or other, that’s kind of what’s happened. I just didn’t expect the teaching to be sales. I did math at University, to a Masters level. Though I would semi-retire to math teaching if I didn’t know what else I’d teach.

But it turns out that while people need help in math, they need even more help in sales. I think I learned from being on the shoulders of giants.

I think I can share a lot of the lessons I’ve learned and the blood, sweat, tears, reading books, getting training, and really tailoring that and then distilling that to help with the challenges that my trainees have. There’s the element of self-fulfilment of helping other people, of changing lives, changing trajectories, and seeing the results.

Jamie: What is the best thing about being in sales performance training?
Theo: As part of the job, you have to constantly learn and grow. That’s something I’ve always enjoyed anyway. Now I have to do it as part of my goals; to constantly get better, to be constantly staying abreast of the market and the latest technology: the tools that have the aide with selling. Honestly, every day I think about going back into the field and dusting off the sales kit and getting back into it. There’s always that thrill of the chase. You’ll always make more money; a lot more money. You miss the challenge, the recognition that you get, and the sense of winning.

On the other hand, with sales performance coaching and training, you can have a lot more impact at scale. You leverage your ability and knowledge 50x, 100x, or even 1000x.

Last year, I conducted more than 150 trainings. I impacted around 3,000 lives last year.

Jamie: Could you be willing to go into a little bit more detail on how internal sales performance trainers are recognized and compensated compared to their frontline peers?
Theo: I would guess some Oracle sales rep in the US make $150k, then the potential of the same again in commission, let’s say, $200k to $300k as a median income. I would think most trainers in the US will probably do a slightly above that base – let’s say 30% above that base, but none of the commission.

Jamie: The difference is in the lack of variable compensation?
Theo:  Yeah. No variable, higher base, but also less stress. No pressure from targets. We conduct trainings nine-to-five. The only real out of office work is extra preparation that you would do for courses. Many people go into this business because they want to help, because they’re willing to take a pay cut, and because they want a different lifestyle. They like the idea of changing lives, kind of all the things I’ve been talking about.

Jamie: If sales training is what I want to do, how do I get there?
Theo: Well, I’m actually, as it happens, hiring for two trainers right now. I’ve been recruiting salespeople for the last almost 20 years now. When you’re hiring a salesperson, you mainly look for communication skills. Ideally, you look for some past experience or at the very least natural confidence and persistence, and you’re willing to work with someone to make up for lack of sales experience.

When you’re looking a sales trainer, you’re adding an additional skill set of everything you needed in sales and a track record there, because they need to be credible in front of an audience. Call it 10, 15 or up to 20 years experience in sales, but then also an ability to present and speak way above what you might only have from doing a normal job and doing the occasional presentation to a team and your boss or your clients. That’s two massive skill sets and then the third one, particularly with Oracle, I need IT experience. Now it’s three. I might take two out of the three if the first two are very strong. I wouldn’t take someone who had just technology and training experience.

There are plenty of learning and development people who’ve been in technology for 20 years, but they’ve got no sales experience, and it doesn’t work. Or they’ve been account managers, but have never been hunters – I won’t take them. I need all three and add to that, they’re willing to take a pay cut from what they would make in terms of their OTE as a salesperson.

Jamie: Would you recommend high-performance coaching to any salesperson?
Theo:

No. I think the most successful salespeople naturally, and surprisingly, are actually very selfish. It’s what makes many people good at sales, number one, they’re hungry. They’re go-getters. They’re successful people. They love the recognition. It’s actually the same reason many salespeople do not make good managers and great managers generally aren’t very good at selling. You rarely get someone good at both. What tends to be the dividing factor is the ability to, or really the desire to, help others at the expense of yourself.

I would recommend most salespeople to not to go into sales coaching or training because it’s not about you. It’s about the audience. It’s about the people under your care. Many times you don’t get that recognition. You don’t get the personal satisfaction of achievement. You only get that vicariously through seeing someone else succeed. Many people also get into sales for the money, and now we’re talking about making less money than what you could do if you’re very good at selling.

Jamie: What do you think makes a sales trainer invaluable to an organization?
Theo: I would say there are probably three main factors that add value. One is to be able to save people time and frustration by giving them training and coaching by people who know the short cuts already, “Don’t do that, I tried, and it doesn’t work.” The second part would be a breadth and depth of reading and knowledge outside of the role, making connections that really land, and really making sense to the people they’re working with. It’s the power of metaphor, power of storytelling, the power of association, where you’re trying to teach one skill or learning point; something that people can connect with and realize that makes a lot of sense. As an exercise – who is the person that you trust most in the world?

Jamie: Wow. My parents.
Theo: Which one of your parents?

Jamie: If I had to choose, my Dad.
Theo: What gives you that trust?

Jamie: I have never seen him not do anything he says he’s going to do.
Theo: How does that relate to you? Has he done everything that he says he is going to do when it comes to you?

Jamie: Yeah. I can only go on my experience.
Theo: If there was something even more than that, what else might there be above that?

Jamie: He has a track record of excelling at everything he does, and while he’s been incredibly busy, he’s been a good father to me. I think that at this point, now that he has more time on his hands, he would go out of his way to do anything important for me or for us as a family.
Theo: So even though he’s busy, he’ll take time to do something for you and the family?

Jamie: Yes. Right.
Theo: So would it be fair to say that he puts your needs even before his own?

Jamie: Not necessarily, but I think he would be willing to. Whether he does or not is a function of what we need and what he’s doing at the time.
Theo: But your sense is that he would be willing to?

Jamie: Yes.
Theo: From his past behaviours and from his past actions?

Jamie: Right.
Theo: What do you think makes your clients trust you, or makes you become a trusted advisor as a salesperson?

Jamie: Credibility, knowledge, and doing what I say I’m going to do.
Theo: It’s exactly the same thing, isn’t it?

Jamie: Yeah.
Theo:

If a client senses that you are willing to put even your own needs before theirs, as soon as they start sensing that, the trust level goes to a new level.

That sense of relating that to a business helps people remember the lesson you’re trying to teach inside a professional business realm. That’s the second part. The third part would be someone they can really like, someone they can really get along with, respect, and connect with. I look for someone that I’d enjoy having for dinner, going for drinks after, and then going on a trip together. Someone you’d want in your team; because the audience would also like him, that would be the third thing. “How do they add value like that?” If someone in an organization is likeable, someone that people naturally magnetized to, someone who is a team player, I think that’s how they really add value to organizations, and I’d like to add them to my team.

Jamie: We’ve talked previously about a candidate who landed a job through social media. What things would you recommend candidates do use social media to get really good jobs?
Theo: Something else that’s going on in my mind is how sales and marketing are becoming more unified. Outside of the job application and the interview, this individual connected with me on social media, and he had been putting out social content, specifically videos of him delivering sales training sessions. It was a very well put together, well-thought-out, and well-delivered programme which showed so much more than I would ever have gotten from an interview. In fact, I hired another candidate, and as part of the application, he attached a one-minute introduction video personalized to the other manager and me that he knew that he was going to be meeting with a very creative message.

It showed their keenness for the job. It showed their credibility, and it obviously showed presenting potential. I don’t think that needs to be specifically a trainer role. I think you could do that for any job and any sales role. It was a very timely, very competent display, and a creative approach to really give anyone who saw the video confidence.

Jamie: More generally, I mean, in terms of LinkedIn as a specific tool, if you were looking for a job, how would you use LinkedIn?

Theo: You can now use rich media. You can attach those kinds of videos inside of your profile, like right below your summary, for example. The easy wins are recommendations, testimonials, and what people are saying about you. Part of my interview is that I want to have at least two references for reference calls.

If someone has made it to the final round, I want to see those references on LinkedIn; to have those ready to go. You’re going to have five or six or 10 references, and as a hiring manager, I won’t go and do 10 reference calls, but I might read every one of those references and come closer to a decision.

Even if one or two of the reference calls weren’t that good, but they had 10 great references on LinkedIn, that might be enough to sway me. I think the endorsements that show your skill sets and those other pieces help as well.

To a lesser extent, affiliations, and interest groups, and I’d say a better-written summary and a professional-looking photo can also help you get hired. I know my boss has actually mentioned that they did not proceed with someone based on their Facebook profile. Generally, it is important what picture you have, and the banner above your picture is a very valuable real estate. That’s the long wide photo or attachment. I’d say don’t be humble. That is the place to list all of your achievements and your awards and qualifications.

Something that I actually look for is the extra qualification and areas of study outside of work. I know one candidate who had done a master’s in AI at Talbot; that’s a three-month course.

They were going the extra mile and had an extra piece of knowledge useful in our industry. That AI experience is very much topical right now. Things like that I think would all help in an application. You can be certain that I’m looking at the LinkedIn profile before choosing whether to interview them.

Jamie: If you were starting blank slate in the process of getting yourself an amazing job in sales, what would you do differently?
Theo: I think something that many salespeople get frustrated with is being unaware of the discretionary part of the commission – not knowing how much they make per sale over and above their quota. That’s really something you need to negotiate in advance. I’ve seen people work really hard, build-up knowledge in a company, and then become frustrated at not getting paid what they’re worth because they didn’t have that extra incentive agreed, and the company had pure discretion in how much of the commission they give.

I think that kind of stuff can be pre-agreed as an understanding, you know, with a direct manager, “Hey, what if I hit my quota and then I exceed it by 100% can we negotiate on how much extra I would make?” In other words, “I double my number. Can we negotiate on a banded approach to commission?”

We’re talking about the conversation you need to have upfront, before you start, and not when you’ve hit the number. There’s also no harm in asking for equity, no matter what. Even in the largest organizations, you might think that you might not get equity, working in a top hundred organization as a sales rep, but; “Hey, can you add an equity target – if I hit this number and this number?”

Negotiate all that in advance. That would be something that I would have done looking back and knowing what I know now about how organizations work.

Jamie: What’s your favourite story from your career?

Theo: Something that comes to mind shows how intense my approach was in pursuing success and finding a way. I remember I had two different prospects. I had accidentally double-booked myself in trial trainings for sales training. One was to the largest insurance company in Singapore, and one was the top-five recruitment and headhunting firms in the UK; their Singapore office. I had somehow double-booked the trainings.

Both of these had taken me the best part of three months to line up. I had to get the agreement of very senior people to line these up, and it would have been really easy to try and choose to cancel one or the other. I felt a certain intensity and the keenness to try and problem solve and find a way. I got to the first one early. I was sitting in a classroom in a skyscraper overlooking the city, and I get a message from the other one saying, “Hey, what time will you be arriving?” It was just one of these moments when your heart stops, skips a beat for a few minutes, you start sweating despite the aircon in the room and the sun’s beating down. I’m just racking my brains trying to think, “What am I going to do about this?” I double-checked, and triple-checked and they are right. I’d made a massive mistake. I thought it was a week after; it was this week. I’d put it in the calendar, and now I’ve got a decision to make.

I sensed the situation on the ground. It was now 11:45am, and there was no one in the room. So I figured out a way. I made a call to that manager from that first training, which was the headhunting firm. I told them, “Hey, no one’s here yet. Can I suggest we actually push this? Have everyone do lunch first? These people look like they’re running behind. I’ll have them all go for lunch, and I’ll come back here at 1:15pm. We’ll do the training then.” After a bit of coercing, the manager agreed. I grabbed my bag and ran across to the other side of the city. I guess Singapore is a small place, but it felt like a long run – it was probably a seven- or eight-minute dash in the full heat of the sun and I made it with a few minutes to spare. Thankfully, with these trainings people aren’t typically early. I had enough time to cool down, get things going, deliver that training, and then do the same run back in under ten minutes and get both done in the same day.

I think it shows that anything’s possible. You can always problem solve. It sometimes takes creativity, but it definitely takes mindset, attitude, and a determined approach

because, in an alternate universe, I could easily have said, “No, that’s impossible. I’m going to have to cancel one or the other.” Either way, I lose business that I’ve worked for over months. It’s a bad situation to be in, but as it happens, it worked out well.

[END]