Jeff Rothenberg, Director, Customer Service at Upgrade, Discusses Identifying Talent, Active Coaching Daily, The Concept of Radical Candor, and More
In sales, you can often find yourself presented with a vastly undervalued opportunity: To learn not only from mentors and colleagues, but directly from the customer. Just ask Jeff Rothenberg, Director, Customer Service at Upgrade, who had a very unique chance to do just that on a large-scale early on in his career.
As manager of business sales for Apple Retail in San Francisco, Rothenberg was able to work closely with a vast range of startups, from two-person operations to enterprises, and discuss their approach to equipping their employees with both the hardware and the information access they need to reach their goals.
Beyond simply selling them hardware, iPads, iPhones and computers, Rothenberg and his team worked with a whole host of founders and CTOs thinking through custom-tailored plans for issues like backup solutions and data, and global device management. They ended up making a mark on the development of these new businesses, and picked up valuable insight on to personnel management, productivity and employee empowerment along the way.
Not only was the experience valuable for his young reps, it had a profound effect on Rothenberg’s own approach to management. In this interview, Rothenberg pulls the curtain back on some of the wisdom he’s gleaned over the years, including the power of radical candor, the usefulness of the 80-20 rule, and what he means by Active Coaching Daily.
The number one thing I look for is that burning to desire to be great. It’s not always easy to identify that, and it’s far more rare to find that inner drive than you would initially think. But when I find people who are essentially driven and motivated to make something special of themselves, it makes my job as a manager so much easier, because they’re fueled to put in the extra effort on all levels.
How does the burning desire to be great manifest itself in an interview?
They’re the type of people who ask me before they even start, “What can I do to get ahead? What can I do to be most prepared before going into training? What specific articles, books or websites should I be reviewing prior to joining?”
When you see those behaviors in the hiring process, what does that suggest about how they’ll act as part of the sales team?
During training, they’re already asking questions without hesitation because they know it’s going to help them. They’re the ones volunteering to give the first demos. They’re okay putting themselves in an uncomfortable situation because they know it’s going to help them in the long run. They’re the type of people putting in the extra effort, coming in early, staying late, Googling questions that they don’t have answers to at the end of their day. You can see that level of desire to be great, and they understand that their first 90 days are really important and so they want to make a mark early and often.
I’m a huge believer in the positivity factor, specifically when hiring salespeople. I want people that look at things glass-half-full versus half-empty. You’re getting rejected in some ways constantly. It can just be a flat-out grind sometimes, so you need people on your team that understand that none of it’s personal, that failure along the way is expected. It just makes you stronger in the long run.
A couple other things I look for are competitiveness and coachability. That history of being competitive and winning in sports or other extracurricular activities is really key. Nothing sucks more than hiring someone that thinks that they know everything.
Many of the best sales reps are people who have a chip on their shoulder. People who have been slighted in the past and are motivated to prove people wrong. I look for a history of understanding what a hard earned dollar is. Maybe they worked throughout college, or they’ve worked from an early age because their family needed the extra income. They’re raised that way. That tells me that they know how to work hard and that money’s important to them and they take the opportunity I’m presenting them very seriously.
Are there particular questions you ask to get at some of the more abstract traits like entrepreneurial spirit, positivity and competitiveness?
I like to ask is ‘What was the first thing you ever sold?’ That opens up some really cool conversation. It gets to how they were raised by their families, and what might have inspired them to go into sales. That type of question has been impactful in pulling evidence of high-performing behaviors out of people.
Tell me about your first few jobs that you had growing up. How old were you? What did you do? What did you learn through those experiences? What worked? Let’s talk about how they have helped you as you continued to grow your career?
What I’ve learned is you need to invest heavily in a strong employee onboarding experience. New hires only have one first day so it’s really important to make it special for them. It’s having little things in order like getting the desk all set up and organized, maybe balloons, take them out for lunch with your management team and some top performers. I also like to write a handwritten note welcoming them to the team and just reiterating how excited I am for them to join our team. That first day, that first week really matters and it’s what sticks with them and can often set the tone for the rest of their experience with your company. That’s really important. A lot of people get that wrong.
Training should not be delegated. Whether you are early-stage or you’ve scaled your team to the point where you need to hire a full time trainer or build out a LMS system, your management should always heavily be involved in the training program. First and foremost, managers need to be the subject matter experts and best coaches, and not just leave it to a trainer.
Even though involving managers in the training can be really time consuming initially, the efficiency gains you get with your new hires is tremendous. If you only get a 1% efficiency gain, that becomes significant over the course of the first 50-plus weeks people work for you. It also sends a really good message to the team that we’re all on this together and I’m really here to help support your growth and your development within our company which is really important to set the tone.
One practice I really believe helps to set the tone is something I call Active Coaching Daily.
Three-quarters of their day, managers should be either sitting side by side in deep-dive individual training with reps, listening in on calls and coaching for one or two specific areas of focus. We would do a lot of live call monitoring. What was nice about that is you could do it sprinkler style, plug in to one rep after another for five minutes, listen to calls, take notes, do some coaching after each call.
Then, lastly, we require our managers to be willing to jump on the phone themselves. We would do things like power hours where we would get on the phone ourselves. Maybe it would be because the energy level was really low on the floor. Maybe it would be to create more competition amongst the reps. Always lead from the front. In terms of building culture, it starts with your leadership team. If we’re high energy and we’re highly engaged and we’re really focused on improving our team around us, that’s going to transfer to our team.
I’ve always believed in radical candor, which involves being very authentic and giving a lot of fearless feedback. We’re going to be the first group of people to high-five you when you close a deal on the phone, but we’re also going to be the first people to give you constructive feedback when we feel you can do better in certain areas. Our managers give a ton of feedback early and often. We want to set the standard for coaching and feedback and the rep’s acceptance of those things is very important to everyone’s success..
We also found individual call listening sessions to be very, very important. These are where we have all of our calls already recorded. We bring calls to a room and bring the entire sales team into the room and listen to the calls for an hour and break the call down, kind of like an NFL film room where you’re going over practices and those and rewinding and fast forwarding. We found that to be very successful and helpful for people. The engagement of our team was really, really strong for those. It would be something that they would request openly and often of, “Hey, when’s the next call session? I really got a lot out of that.” There’d be a lot of natural dialogue amongst each other which was awesome too.
We really encourage transparency with team vision, goals, measurement and progress. It’s like bringing your team along for the ride, creating that culture of people feeling empowered but being well-informed. It creates a culture of people feeling really a part of the team, a problem solver, a business owner. We build that culture of trust and idea sharing early by asking questions like ‘How we can do better with our training?’
Did you experience any pushback or conflict that arose from people feeling singled out or embarrassed in front of the group?
The key is having an open attitude. We’re not putting people down on the call or laughing if they make mistakes. We’re in this meeting room with respect and a sense of professionalism in trying to help our peer out. I think having that baseline professionalism and respect amongst your peers without joking or snickering or any of that is really important but my whole thing was if you’re going to have a hard time with us reviewing the call in front of your peers for your improvement, then maybe sales isn’t the right thing for you.
We were pretty lucky. We didn’t have a lot of backlash with that. Again, it was really coming from a supportive angle. People really wanted to help other people out. Then, also, you have those people who think that they’re better than what they really are on the phone or they don’t understand why they’ve gotten a customer complaint. Sometimes, playing a call like that, they hear themselves, their tone of voice or their attitude in how they handled the customer, when you’ve been telling them these things, that can send a message that’s pretty powerful for that rep.
I know this is really simple, but you need to set a recurring one-on-one that works for you and your employee and stick to that as consistently as possible. Don’t move the one-on-ones on every week to different days and times just because you think you’re so busy. Oftentimes, employees will come off like it’s okay to them that you’re moving things around but it’s really not okay. It’s really disrespectful to them and a big indicator that you don’t value your employee’s time and their voice enough.
Keep in mind, if your people are engaged and they want to improve every week, the one-on-one with their manager might be the highlight of their week because it’s the only time that they get some solo time to voice their concerns, their feelings, their ideas and really talk through different methodologies for their improvement. Don’t push these one-on-ones around. I think this is a common error for particularly new managers but managers in general.
I try to live by the 80-20 Rule. Let the direct report do 80% of the talking and you do 20%. Another way to think of it is the ten to one rule. Ask questions at a rate of ten to one of giving answers.
I personally hate wasted time in one-on-ones. We’re all busy, so try and maximize time as much as possible. Personally, when I first started managing people, I had a few of those awkward, ill-prepared surface level one-on-ones. I made the mistake of not being prepared enough and also not expecting my employees to prepare themselves enough. From my personal standpoint, I try and come prepared to the one-on-ones having reviewed my notes from the previous week as well as looking at the latest metric from my managers, team KPIs or their individual sales rep KPIs.
I also ask that my reps or my managers submit an agenda every week for the one-on-one beforehand, so I can review that as well. I want my direct reports to put thought into our weekly one-on-one agenda so we’re not just sitting in a room with each other asking about the weekend. We can really hit the ground running.
There are three parts to how I structure one-on-ones, the first part being really framing the career progression that they’re working towards. How are we tracking towards your career goals, both short term and long term? The second part would be really drilling down into the performance. That’s really what drives career progression, so that’s really important. Then, the third part’s really drilling down into the metrics which in turn drives performance like net promoter score, customer satisfaction, activity level, pipeline created, coaching moments, things like that.
In my time at Lending Club and Apple, I worked with a younger group of sales reps. They haven’t yet seen what outstanding looks like, how promotions happen, what being a great leader means. It’s really important to consistently communicate to them the point of doing all these repetitive tasks. It has to go beyond just starting at the bottom and paying one’s dues. I try and make one one-on-one a month really focused on career goals.
It’s important to come prepared with a great agenda, and to get the team to contribute to the agenda. When it’s just me trying to create an agenda myself, A, it’s a heck of a lot more work for me to come up with all the ideas and B, the engagement levels aren’t as high as when the agenda is created by the team.
I’ve had a lot of success in people teaching specific subject matters to employees in these meetings where not only are they learning on a deeper level but having to teach it out to others but they’re educating others, their peers, maybe in a more effective manner than coming from their boss.
I also like to do ice breaker questions to get everyone involved in opening oneself up, contributing, smiling, laughing and bonding with their teammates. Some of the things I used to ask is like, if you can have a superpower, what would it be and why, what’s your favorite childhood television show and why, goofy, off-the-cuff questions like that. Just to start the meeting out with people smiling and contributing and laughing opens the room up and gets people a little bit more awake, particularly if you have a morning meeting.
I like to show what greatness is also with a sales call of the week, chosen by the leadership team or by rep submission. It recognizes that person that had a great call but more importantly, it shows the team, specifically younger sales reps, what greatness is and that even greatness still has areas for improvement.
Often in our team meetings, we will review a great article that I came across during the week. We’ll break down that article. What can we learn? I’m a big fan of playing podcasts on specific topics that are applicable to the group, to really teach your employees how to become better people in life. Some of those podcasts like Lewis Howes has a podcast called The School of Greatness or there’s a podcast called The Charged Life with Brendon Burchard. It’s really fun and effective to play 10 minutes of a podcast and then break it down and talk as a team about what we learned.
I’ve also been known to mix it up. We did book clubs. We’ll take a book every quarter and we’ll review each chapter weekly for about 10 or 15 minutes as part of our team meeting. That’s where everyone’s reviewing and contributing and sharing their personal learns. We’ve even done crazy stuff like meditation training in team meetings to talk about stress reduction, focus, topics like acceptance, gratitude and appreciation, generosity, patience, happiness. We’ve also had success in bringing different people in from all over the company once a month for 15 or 20 minutes to explain what they view, what their group does, how they grew their career into what it did, any life advice they may have in some open Q&A time. The team appreciates bringing in different people from all over the company to learn more about other groups.
I think one of the big things that I wanted to do … I always believe the most intelligent thing you can possibly do in your life is to grow because when you focus on your own growth, even though initially, it can seem like a really selfish thing, you actually transform everyone you come into contact with. By working on your own growth, wherever you feel directed to do so, whether it’s improving your health, improving your relationships, improving your finances, improving your spirituality or really taking charge of your career path, you become a different person.
You transform yourself and in the process of transforming yourself, you actually influence other people in a whole different way than you might be influencing them right now. You have lifted the people around you. You serve as a model of the people around you. You serve as the example of how they can uplift their life well, of how they can create that change in their life. By working on your own growth, you’re actually making a massive contribution to the lives of other people. I can tell you from a personal standpoint, that’s something that’s really amazed me as I worked on my own path of growth.
That’s generally how I feel about personal development and growth. We’re trying to incorporate a lot of that learning into our team meetings. It’s the most basic way. It’s like when you think about it, you’re not just trying to build, you’re not just trying to create great sales people or great customer service people. You’re trying to create great people. A lot naturally surfaces from focusing on that type of development of your people professionally and personally.
I think metrics matter because current performance ultimately drives career progression. In my one-on-ones, the last thing we reviewed during our one-on-one, I want my direct reports to have a good idea of exactly what they’re doing great at, and maybe a few things that they need to improve upon and how they can go about making that change. I also think it’s important not to just leave a one-on-one giving your direct report a list of things to do on his or her own. That’s part of it, but also, as a leader, you need to ask yourself, “Have I given them all the tools and resources they need in order to be successful?”
In my experience, it’s the work you put in after the one-on-one that makes all the difference. In my case, I would often schedule a time in my day as a follow-up to a one-on-one to sit side-by-side with the rep or to listen to calls with the rep and coach accordingly. If they were, for example, struggling with their recurring objections on calls or their call activity was very slow to start the day. Maybe they were only making 30 calls between 8:30 and 11:30 in the morning. I would then schedule some time over the next week to start my morning with them, set some goals and show them that with the right organization and structure in their day they could double their goal from 30 to 60 calls.
At the team level, I like showing the entire team’s rankings in team meetings so everyone can see who’s at the top and who’s at the bottom. In some ways, this might sound bad but I want my bottom performers to feel the heat and I want them to be okay with getting uncomfortable with not performing. Losing really doesn’t feel good. You should be asking yourself hard questions to find out what you need to do better. And I want to really highlight my top performers. This is what excellence is. I think naturally, that opens the floor up to collaboration between top, middle and bottom performers, which is important to me in team meetings.
I am personally a big fan of skip-level meetings, meeting directly with my manager’s employees that report to him, to assess how well my managers were communicating and performing. That way I get feedback from the floor that I can share with my managers directly. It also shows our floor reps that I‘m taking significant time out of my week to meet with them and hear how they’re doing, what’s going well, what we’re struggling with and what we can do better. The floor always felt really supported, which is big.
At Lending Club, we went from having a five-person team when I first joined to having over a 70-person team. Your communication changes. It’s a lot easier to communicate with five people versus 70 people. Obviously, our communication plans had to change significantly as we started to grow. I think some of the things we did to make sure that we’re communicating well with our staff is again, have that open culture where we would ask them questions in their one-on-ones or team meetings how is this form of communication working for you, do you feel well-informed, where are we missing things, getting feedback from the team, having the skip level meetings.
One of the things that we realized is that as a management team, there was so much great information that we were sharing amongst each other behind closed doors but we weren’t sharing enough with our teams on the floor. Say for example, I had a monthly PowerPoint presentation that I put together for our CEO and COO that I would present to him on the state of our sales business. I would share that PowerPoint, that same PowerPoint to our sales team in our meetings as well and just keep them informed and empowered by that information.
We also created a monthly newsletter where we recognize top performers, top performing teams. We give team updates around performance. We also highlighted specific changes that we had made in the past month based on their previous feedback to let people know that, “Hey, not only did we hear your feedback loud and clear but here’s the progress that we’ve made in making positive changes based on your feedback.” That was really well received. Those were some things that worked really well for us as we scaled from five to 70 plus people.
I’m sure a lot of people are familiar with smart goals but I really believe in them. When I refer to smart goals, what I mean is that it’s got to meet a couple criteria. First is it’s got to be specific. Your goals have to identify exactly with what you want to accomplish in as much specificity as you can really gather. It needs to be measurable. Goal management is like if you can’t manage … You can’t manage what you can’t measure. If possible, try to really quantify your results. You really want to know absolutely positively whether you can hit the goal or not. They’ve also got to be actionable. Every goal really should start with something like an action verb like run, eliminate, finish, quit versus a go-to verb like am, be, have. Then, you want to make it realistic. You really have to be careful.
A good goal should stretch you but you have to add just common sense and reality. I personally like to go right up to the edge of my comfort zone and then step over it. If I’m not out of my comfort zone, then I don’t really think I’m thinking big enough with goals. Then, lastly, time bound. Every goal needs to have a date associated with it. When do you plan to deliver on that goal? Instead of saying, “Hey, I want to lose three waist sizes,” it’s like, “Hey, I want to lose three waist sizes by October 31st.”
There’s huge power in writing your goals down even if you don’t even develop an action plan or do anything else. Just writing your goals down is really key. The reason for this is when you’re writing something down, you’re actually stating your intention and thus, you’re setting things in motion for yourself. I don’t think people initially understand how powerful that is. One of the things that I used to do is I would literally make the team write their goals down and print out and frame it on their desk so that it was in front of them every day. We would sometimes take it into team meetings and people would reiterate what their goals where. It’s a sense of positive affirmation on goal setting that was really key and visit it in front of them.
Also review them frequently. While writing your goals is powerful, the real juice is really in reviewing them on a regular basis. That’s really what turns them into reality. Then, it’s like when you review your goals, you need to ask yourself what’s the next step I need to take really to move forward with this goal. Then, I’ve always been a proponent of sharing your goals, and do so selectively with people who are going to help you accomplish them. This creates this accountable structure for achieving your goals where people can follow up with you and also help you achieve your goals together.
We use something called OKRs which is really a simple spreadsheet. OKRs are objectives and key results. Every employee would put in four different quarterly goals, three of them being professional and one of them being personal and highlight the action that they’re going to take to achieve those goals. Then, we would share that spreadsheet over the cloud with the entire company and make sure we can read each other’s. That will create that structure of accountability as well. It’s just pretty basic that we use OKRs and it was something that we could review weekly, monthly, quarterly, whatever case we wanted to review and really track our performance against us.
What are the qualitative aspects of performance you like to pay attention to that are hard to measure?
First would be your personal effort. There’s a correlation between a rep who regularly smashes his or her quota, and doing the little process things that sales managers preach for the reps to do. Hitting your quarterly goal is super important but it’s also important to follow the sales process. For instance, how does the rep spend his or her time when not on the phone? It’s been very frustrating working with some reps who, during their downtime, they’re goofing around a lot, they’re surfing the internet, watching YouTube cat videos or something. Others might be talking to managers about trying new approaches, organizing their upcoming to-do list or maybe reading a chapter or two in the sales book. Failing to plan really is, as they say, preparing to fail when it comes to making sales calls. It’s also imperative that sales reps are delivering a really captivating and valuable online presentation when giving demos.
More tips to master managing intangibles.
A key to success is the desire to learn new things. In my experience, the best reps are never okay resting on their laurels. They know that the minute complacency sets in, they’re going to slowly but surely lose their standing as the top rep. They’re always trying to stay sharp by learning new skills, honing on old ones. That continual investment in learning is really key.
Second is knowledge. Does a sales rep understand your product inside and out? Can they answer any question both from customers or internally about your products? When new features are added or introduce, do they make the effort to learn about those new tools? Can they communicate your product’s value proposition against the competition? It’s being fully aware of your competitors, their products and perception in the industry at all times.
Then, I think the third one I want to hit on is personality and attitude. Does a rep get along well with the rest of the team? This doesn’t just mean hanging out for a few beers and laughs on a Friday afternoon. It’s really observing to see how helpful the rep is, how many inside jokes can they share with the rest of their team, how willing are they to go out of their way to help pick up a struggling rep. Teamwork is a really critical part of sales success. You don’t want a team of lone wolves on your team.
Lastly, is the rep willing to accept responsibility when things don’t work out? A rep who steps up and is willing to take responsibility publicly is a strong sign of character. These types also tend to solve problems on their own instead of asking 10 million questions even about the littlest things.
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This interview has been edited and condensed for length and clarity.