April 25, 2024

Between Two Hires with special guest Misha McPherson


Episode Highlights

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In episode 5 of Between Two Hires (The Subtle Art of Not F#*ckin Up Your Team), Misha McPherson, a sales enablement expert, and Tom Wilkinson discuss the importance of hiring for sales teams to include the need for a focused hiring process, strong communication between sales and recruiting teams, effective pre-boarding and onboarding, and asking insightful interview questions to assess candidate motivations.

Episode Transcript

Misha McPherson, nice to see you. How are you doing? I’m so good. So good to see you as well. Good to see you too. Actually, this has been a long time coming. I’m glad you’re able to join us and had your partner in crime, Mr. Cameron on not so long ago. So this wouldn’t be, it wouldn’t be one for us if you didn’t get an opportunity to share some of your knowledge as well.

And so we go way back. I think we first crossed paths at ShareRoute. And we’ve also had- many moons ago. Yeah. But we’ve also had the good fortune of having you speak at least one of our SKOs. I believe, if I’m not mistaken. And I know everyone gained a ton from that, including myself. So I’m very excited to have you join today.

I don’t know if you fancy just giving everyone a bit of a intro to yourself and what you’ve been up to and what you’re working on. Absolutely. So I’ve been in the tech space for I think it’s going on something like 25 years at this point, a ridiculously long time. Lucky enough to be born into the Bay Area tech scene.

And so my entire career has been spent here and my entire career has been around sales. So hiring is one of my favorite topics because unless we hire the right people, it doesn’t matter how great the product is, it doesn’t matter how great the marketing is, we have to have a great team. So I love this topic.

I’ve spent time both selling, myself being a sales person. The majority of my career, last 15 years or so has been around sales enablement. So I work to scale and enable sales organizations to be successful. I currently run a consulting company called Humble Grit Sales, where I do fractional sales enablement, and I specialize again in companies that are kind of that, you know, that scaling stage they’re trying to grow, they’re trying to figure out

what do we need to put in place in order to make sure that we can be successful in every stage of the company? Strongly, strongly endorse and recommend Humble Grit Sales and Misha McPherson. All right. I’m excited to get into it. So yes, let’s start with, if we could,


what are the biggest mistakes that sales teams are making in terms of hiring that you’ve seen? So this is going to sound so basic. It’s going to sound so basic, but this basic thing is happening and it’s been driving me nuts for decades at this point. There is a conversation that’s not being had. So what I typically see is you hire this great sales leader and this great sales leader brings in the people who have been in his network

and have been successful in the past. But we’re skipping a step. We’re skipping a huge step. And especially in earlier stage companies where we’re all learning at the same time. There’s a conversation that really has to be had on who is the person that we need to hire, right? What is the profile? What is their skillset?

What’s the personality? What are they going to do for a younger, earlier stage company where there’s no marketing collateral? What are they going to do when our ICP is X this quarter and we change it to Y next quarter, and we might go to Z the quarter after that. How are they going to respond to those changes?

You know, have they worked at big companies? Have they worked at small companies? Who are they? So that is a serious conversation that I think often is had in like a 10, 15, 20 minute conversations had, I think that actually has to be a longer conversation and really thoughtful.

And then that has to be shared back to the recruiting team. Another thing that I’m seeing is that the recruiting team and the sales team is not as tight as it needs to be. Sales often looks at recruiting as a separate engine. It’s the same engine. You really have to have the- recruiters really have to understand exactly what the salespeople are doing and what makes their job easy, what makes their job hard in order to really find those people.

So sales has to invite recruiting to the table a lot more. There’s a lot more that I could add on to it as well, but that’s the thing that drives me nuts. We need to have a deeper conversation of who is this person that we’re looking for, right? And what are the questions we need to find, that we need to ask in order to determine if they’re the right person.

I’ve got one more thing. This is also driving me nuts. Recruiting process is so long. Why? Why is the recruiting process so long? I can’t tell you how many times I’ve seen an op, like it will open up and next month, next month, next month, we still, we’re still hiring for that role. Why? So I think that if there is more conversation upfront, if we are really thoughtful about what specifically we’re looking for so that we can have less people involved in the hiring process, do we really need six, seven, eight people involved in the hiring process?

Do we really need to have four different stages of interviews in order to determine if this is the right person? We can shrink the time to go great candidate to the hiring into a new hire spot. So we can determine, do we have the right person in place? Yeah. Couldn’t agree more. Very good points. Oftentimes I have found that if companies viewed their recruiting process the same way that they view deals internally, they would be hiring more effectively and quicker and better individuals. It’s a shame that there is that disconnect.

Yeah. Okay, moving on.


In keeping with processes, what to you makes for a strong hiring process? So I think that there’s a few things that are really important. I think making sure that every person who is part of the interview process really understands what’s their purpose. And by the way, that there’s an alignment so that the hiring manager, the CRO, for example, really agrees with every single person who is part of the interviewing panel, really wants those people to be part of the interviewing process, I think is really important.

I think making sure that every person really understands what questions they should be asking and why they’re asking those questions. I think that makes for a really strong process. I think one of the things that I see too often is that people get asked to be a part of the interviewing panel, but they don’t really know why or how or what they should be doing.

And they don’t really feel like they have a voice in the interview process, right? If they really dislike somebody or like somebody. So making sure that you’re really concise with who is actually part of it. I think it’s really important for candidates to hear from other people who are actually in the role, right?

So that they can have those good conversations as important conversations to understand, is this a right fit for the candidate as well as is this the right fit for the company. That makes for a really strong process. And finally not overselling. Right. So it’s really easy, especially in sales, it’s really easy for us to oversell.

You’re going to have this amazing book of business and yeah, you’re going to have to do a little bit of prospecting, but let’s look at this industry, let’s look at the opportunity, let’s look at all these amazing things. It sets this expectation that selling is going to be easy. And today, selling is not easy.

It really is not, right. So let’s be honest with ourselves. Let’s be honest with our candidates that, hey, you are going to be responsible for prospecting X amount of your book of business. And what that means is this, you’re going to have marketing backup, or you’re not going to have marketing backup.

You’re going to be expected to pick up the call, pick up the phone, or you’re not expected to pick up the phone. Let’s be really, really clear about what the actual opportunity is so that they can also help remove themselves from the process if they’re not up for it, right? I think that honesty really helps us figure out on both sides, is this the right fit for both the candidate and for the company.


So let’s say that we now have implemented some of these focus areas to create a really strong hiring process, what does happen next in your view? Yeah. So I think that, you know, and this is of course going to be something that’s near and dear to my heart. But the next step is pre-boarding and onboarding, right?

And so in terms of pre-boarding, what happens between the acceptance offer and the start date? And those days or weeks are really important, right? There are small things that are not expensive that we can do as a company that’s going to make that experience so much better. For example, almost every company is going to have a new hire buddy, right?

Like that’s standard. That’s easy, right? Connect them before the start date just to say, hi, I’m going to be your new hire buddy. I am so excited that you’re coming on board. Feel free to reach out to me if you’ve got any questions between now and the time that you start and you and I will be having a virtual coffee or a real life coffee on day one.

Right? Those little things. Hearing from the CRO, if the CRO hasn’t been a part of the conversation, if you’re an earliest, early enough stage company hearing from the CEO, you know. So having some of those, like we’re excited, hey, if you were interested, there is no expectation, but if you were interested, here’s a couple of things that you can look at before you start. Your onboarding starts the day that you start.

But if you are curious in advance, here are some of the things that we are thinking about, talking about, in terms of the ICP or in terms of the industry or in terms of thought leaders that you can start following today. These are some things that can help get you set up for success.

Always be very careful legally. You can’t require people to do things before they start. But if I am a really hungry sales rep, I want to hit the ground with a headstart.


And then on onboarding, one of the biggest mistakes that I see continuously is that there is a misunderstanding of the word ramp. When sales ops often talks about ramp, what they are talking about, or finance talks about ramp, what they’re talking about is, hey when we change

how people get paid out and that is not a ramp. That is not ramp. A ramp is when that person is actually going to be successful in going through and selling their book of business. When we know that we have the right fit, when they know the messaging, they know the ICP, they know the sales process, et cetera.

So let’s be really clear about what do we mean when somebody is done with ramp, when somebody is actually prepared to be a full member of our sales team. Sharing that- this is so obvious, sharing that with the rep, right? We know that you’re going to be successful when you know these things, when you are capable of doing these things, and when your results look like this.

Then you know that you are off to a good start. So sharing those conversations, creating data that they can track and you can track so that you can both see, yes, we are on the right track, or hey, we need some additional coaching on this area. It’s very unsettling as a new hire when you don’t know if you are successful or not.

And so anything that we can do to make sure that they know what is working and what’s not working is actually going to benefit everybody in the end. Yeah, I love how you put, pre-boarding. It’s an area that I think makes such a big difference to someone joining a company. And first hand, I also know that, that period of time between the individual accepting the offer and day one is pretty crucial.

And given there are a lot of other recruiters, hiring managers, sales leaders that will be trying intensely if you’re good to bring you on to their company, that period of time is crucial. So the engagement with that individual and the company is so very important. So nicely put. Well let’s get back to hiring for a bit here because, well, why not?


What do you think would make the relationship between sales leaders and recruiting stronger? You touched on it earlier and I’d love to get your take. Yeah. So again, these are little things that are so easy to miss, which is why I think that they’re so often missed.

But there are all these opportunities to bring sales together that recruiting is often not brought to the table with purpose for. I think this is especially interesting in this kind of new world of are we working fully remote? Are we hybrid? Are we in office? And so making sure that that

culture is understood and that’s incorporated into it. But when do we bring salespeople together? We bring them for, as an overall, or we bring them together for QBRs, we bring them together for kickoffs. We bring them together for happy hours. We bring them together for all these things and recruiting is not.

Right? And so I think it’s sometimes it’s the little thing. QBRs and kickoffs are the two times where I really feel like recruiting should be a part of it. Why? QBRs, you know, a good QBR, you’re really going to be talking about what worked and what didn’t work. Right. Sales leaders often leave those QBRs with projects that we have to undertake. You know, hey, it looks like we’re selling to the ICP, but we don’t understand the ICP or we’ve got the wrong messaging for the ICP or, hey, we haven’t considered, like we have hired all these people from a different industry and they don’t know this new industry.

All of those things turn into, okay, right, as we’re going through hiring we actually, we should start experimenting with hiring from within industry. We should start experimenting with people who came from larger companies where they had stronger sales enablement programs and they were taught sales skills, whatever it is, right?

So QBRs I think are really are great because you get a really good touch on what’s working and what’s not working within your organization, that recruiting can take into place as well. And then same thing with kickoffs. Kickoffs, recruiting should always not just be invited but have them play a part in it so that they are

talking not just to other recruiters, but they’re talking to the sales people, hey, what’s working, what’s not working? Hey, what do you wish you had known before you started? I was your recruiter. What do you wish you had known me first? Right. And so that at the end of the day, whether you ask a sales leader, a rep or recruiter, what’s the number that we’re trying to hit?

Everybody’s got the same answer. What are we trying to accomplish? Everybody’s got the same answer on that. Nice. I like it.


In keeping with interviews, do you have a secret or unconventional interview question or tactic you use? Yeah. So the question that I always, that I love to ask, and it’s funny, I don’t know if many people ask this question because it often seems to throw people off a little bit is, I typically interview salespeople.

I ask this question regardless of what this role is. So what brought you to sales? And I usually get kind of a you know, I was an English major. It was the only thing that was hiring. Great. Okay, cool. That’s just the kind of a warmer sort of a question. It’s fine. I’m not, I really care about that question, but I care about is a follow up question.

What keeps you in sales? What do you enjoy about it? Why? What is it? And there is a tipping point. What I hear, I hear a lot of, well I’m here for the money and I have no problem with that answer. You are here for the money if you are in sales, that is true.

But the really special reps will then connect it to something else, right? They will either say, like, I’m in it for the money because I want to provide my family with stuff I didn’t have as a kid. Or they’ll say, I do it for the money because of X, Y, Z. Or, I am here for the money, but I also really love the challenge of sales.

It’s the next thing that they tell me that I think gives me a little bit of the insight into is this just another job for them, which is okay. But- or is there something that’s going to drive them to stay for one more call to work just that little bit of extra, that’s going to take them from a B player to an A player.

That’s going to be, take them to just almost hitting their quota to overachieving overachieving their quota, right? So that’s the thing that I always like to ask. Very nice. I like it. Okay, so then let’s sum things up here.


What’s one thing you want to see in early stage recruiting? Focus. Focus.

Oh my gosh. I want to see more focus. And this is not like- this is a focus that needs to come from the top down from the company. Yeah. What are we focusing on? Right. So that’s the first part. I really like, I am so excited when I hear the same answer from multiple people within a company.

What I often hear are totally disconnected answers, which always worries me. Makes me very happy as a consultant. Makes me very unhappy as an employee, right. So focus is so important. And the second part, and I think that this is so easily missed is then the communication, right? It doesn’t matter if we all have the same answer

if we’re not communicating the why behind it, the how behind it, all that good stuff as well. So really communicating between the different groups, between the recruiter and the candidate, between the candidate and the hiring manager, between all the people that need to be involved, keeping that line of communication clear

and open and ongoing, I think is- I have to say, as a candidate, you never forget a great hiring experience and you never forget a horrible hiring experience. And there’s so much opportunity to take a B plus hiring process to an A plus with a little simple things.

Amazing. Misha, so many nuggets and some of the simplest I think are the most effective and thanks for sort of summarizing those and bringing them to the forefront. So I hope a few individuals will be able to gain something from this. I was just going to say to kind of to wrap things up, maybe finish the sentence.

If you are, you should reach out to Misha and Humble Grit Sales. Yeah. If you are a company that is currently trying to figure out what is your scaling process and how do you build early stage sales enablement within your organization, call me. I take very limited clients. So it’s very, very limited to what I work with, but the kind of the problem statements that I most commonly see is we don’t know what to do about onboarding,

we don’t know what we’re doing about sales process, we don’t know what we’re doing in terms of what sales enablement should look like and we need to hire in a sales enablement leader. We don’t know how to hire that person. So all of those things are things that I’ve been doing for a very long time.

And I love to work with. I love it. You are an expert in your trade. Thank you so much for joining and for sharing these nuggets here today. Thanks again, Misha McPherson. Good to see you. My pleasure.

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