Scott Trench of Biggerpockets.com: Giving Feedback; How To Be Honest Without Being Hurtful

Giving honest and direct feedback is an essential function of a leadership or management position. There are many methods and techniques for doing this, and this is a skill that I as a CEO continue to work on developing. I remember how important it felt and how impressed I was when I received my first formal performance evaluation. I immediately promised to deliver the same work product to my direct reports in the future.


As a part of our series about “How To Give Honest Feedback without Being Hurtful”, I had the pleasure of interviewing Scott Trench.

Scott Trench is the CEO and President of BiggerPockets.com and has dedicated his career to helping ordinary Americans build wealth in part through real estate investing. Since joining BiggerPockets in 2014, Scott has authored wealth-building book Set for Life and joined Mindy Jenson as a host of the BiggerPockets Money Podcast. An active real estate investor in the Denver market, Scott currently manages a private portfolio with about $1.5M in real estate assets under management and holds his real estate license as a CO broker.


Thank you so much for joining us Scott! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I joined BiggerPockets in 2014 as the third employee and a personal fan of the company’s mission — making real estate investing accessible to ordinary Americans. Over the past six years, I’ve taken on an increasing level of responsibility within the organization, ultimately accepting the job of CEO when we brought on private equity partners in late 2018. During my tenure, I have focused on leadership and living out the company’s mission, including investing in real estate, stocks, and other assets privately, living frugally, and building towards a position of permanent financial freedom.

What do you think makes your company stand out? Can you share a story?

Our company stands out because we are helping ordinary Americans working full-time jobs achieve a state of permanent financial independence early in life. When you help someone become a self-made multimillionaire through hard work, self-education, and discipline — and help them achieve this in their 50s, 40s, 30s, or in some cases 20s — the world is their oyster. They go on to change their community and become major players in solving world problems.

My favorite example from this past year is a veterinarian from Pennsylvania I met. She was able to achieve financial freedom in the past year and spends her time now bringing attention to the enormous financial burden and relatively low incomes of veterinarians. Her purpose now is working to make the decision to become a veterinarian more economically viable for more people.

Can you share the most interesting story that happened to you since you started your career?

There are countless stories internal to work, my progression, and the hundreds and hundreds of people who have achieved financial independence through real estate that we have featured in books, podcasts, etc. Perhaps a funny one might be helpful here, though.

Our team at BiggerPockets has a bit of a healthy obsession with Smash Mouth. We’ve probably played “All Star” 1,000 times over the past three or four years in the office — I honestly think that this is very reasonable approximation. Well, one day we get a letter and a delivery to the office. It’s from a guy named Sean Hurwitz — Smash Mouth’s guitarist. Sean tells us in his letter that he is a big fan of BiggerPockets and a real estate investor. Sean learned that we were huge Smash Mouth fans, and he sent us a drum signed by the band and 20+ guitar picks used by him over the years. Turns out that while we were big fans of Sean and Smash Mouth, he was also a fan of US!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’ve made plenty of mistakes, so many that they all blur together. From the very early days, one that stands out is that I once accidentally sent a mass blast email to our entire email list that was still in draft form. I also made a lot of public mistakes in my early writing for our blog — and plenty of seasoned, smart, self-made multimillionaire real estate investors were quick and direct about my errors in public comments on those blog posts!

What advice would you give to other CEOs and business leaders to help their employees to thrive and avoid burnout?

First, I think that application of the 80/20 rule is essential to long-term success. I have to constantly reprioritize my task list, and go after the next most important thing at all times. I think that a lot of folks who like to see things through to completion may get frustrated as they move to more senior executive roles in startups or small, fast-growing companies. For me to be effective, I have to be ready to pivot to the next task when the 20% of the work that delivers 80% of the value has been accomplished.

Second, another key for me is separating work and home life. While I might work a little later into the afternoon and evening, when I am done with work for the day, I am done. I sign off and don’t check my email or messages until the next workday. While there are some notable exceptions and occasions that call for me to drop what I’m doing and sign back on after hours, these are remarkably rare. When I am on, I’m on — but not 24/7. There’s always another $5,000 to be made here or $10,000 activity there. But if you try to do everything that can conceivably be done to move the business forward, you’ll go insane as CEO.

Third is commanding my calendar and setting aside large chunks of time to have open. I try to arrange all of my meetings to occur back-to-back and to leave large sections of time open for more work. This can’t happen every week, but most weeks, I will have a cumulative 8–10 hours between 9:00 a.m. and 5:00 p.m. of open time to focus on the most important long-term work that needs to get done.

The workload is theoretically limitless, all of it is potentially worth thousands of dollars per hour, and the most important next thing (at least the most important seemingly urgent next thing) is constantly getting reprioritized. One has to stay focused on the key things.

How do you define “Leadership”? Can you explain what you mean or give an example?

I think leadership is aligning a group of people towards a common goal and instilling a shared vision that enables everyone to bring their full talents to bear on moving as directly towards that goal as possible. I’m not sure I’m an expert on this quite yet. Internally, we communicate the shared strategic plan a few times a year with the team, we discuss segments of it weekly at our open metrics reviews, and I discuss key values and expectations with team members during onboarding and during skip level meetings. I think that this is a great question and frankly, an opportunity to self-assess about whether I can’t do a lot more here to really study the concept of leadership, evolve my definition of it, and perpetually set out to improve against that.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

Our business grows at a rate of give or take 50% per year. This means that every week (grossly simplifying the nature/math of compounding), the stakes get about 1% higher. The days of getting stressed about the next big milestone are never completely over, but the context of “stress” is an adaptive one. My normal is this environment. I’m sure it would be very stressful to go immediately from entry-level employee to this role, but it wasn’t like that. It’s been a 1% acceleration of the stakes of my role per week for years in a row. There are the rare days where the stakes seem completely enormous and where there are no “win” conditions or options that result in a positive outcome, but our strategy and core competitive advantages thankfully allow for those days to be extremely rare and tactical in nature.

Every day, the stakes get just a little bit higher. That’s the norm for me. And because that’s the norm, it’s another day in the office — not particularly stressful or not. Or at least no more so from a relative perspective than my first job as a financial analyst. I think that I was equally nervous going into my first performance review as I was going into my first board meeting. My meetings with our board are no more difficult or stressful for me than delivering difficult feedback to a key employee, working through a tricky customer situation, etc. Further, the nature of the job is to have so many high priority items on backlog that I am just a little too busy to get nervous, overly stressed about a decision, etc. For me, stress comes when I have a single high stakes decision or event that I have to get right and have to plan for meticulously. When I have weeks, days, or hours to prepare for one thing and little else, that causes the nerves. Luckily, I never have the opportunity to get that worked up about a single decision!

So, overall, the way that I remove the stress conditions are by working with the team to sustain a high rate of growth, attempting to personally develop faster than the company’s rate of growth, staying busy, knowing that there are a million things that I am not doing — and being OK with that. I can rest easy knowing that many of my bets will be wrong, but I have a strong and cohesive “why” and framework for all of my decisions, and the overall net effect is to the positive.

Every day is challenging, intense, and requires my best. Probably like every other human being, I’m at my best when I eat right, exercise intensely, and get a good amount of sleep. I am very diligent about this, as well as organized and clear with my daily planning and personal/business goals.

Ok, let’s jump to the core of our interview. Can you briefly tell our readers about your experience with managing a team and giving feedback?

Giving honest and direct feedback is an essential function of a leadership or management position. There are many methods and techniques for doing this, and this is a skill that I as a CEO continue to work on developing. I remember how important it felt and how impressed I was when I received my first formal performance evaluation. I immediately promised to deliver the same work product to my direct reports in the future.

This might seem intuitive but it will be constructive to spell it out. Can you share with us a few reasons why giving honest and direct feedback is essential to being an effective leader?

If you don’t give honest and direct feedback, you lose credibility with your team, and if you are unhappy with a team member or feel that they are not performing, there is no greater disservice than to allow them to think that everything is fine. It’s not fair to you, it’s not fair to the rest of the team, and it’s not fair to them. They can’t develop if they don’t know there is a skillset or performance gap.

One of the trickiest parts of managing a team is giving honest feedback, in a way that doesn’t come across as too harsh. Can you please share with us five suggestions about how to best give constructive criticism to a remote employee? Kindly share a story or example for each.

Frankly, I don’t know if I’m a master at this. I’m very direct, and I know that in the past week alone, I’ve probably come off as too direct or forceful in my appraisal of a work product. I think that sometimes, if I think a work product is not very good and voice that opinion, there’s no way that this will come across positively. I just hope team members don’t take it personally and understand that my problem is not with them as individuals, their skillset, or fundamental body of work (otherwise I would highlight that in an evaluation), but rather with a tactical decision.

First, perhaps a useful construct for this is the DISC profile. I am a very high “D,” meaning that I’m very direct, quick to make decisions, and like to be efficient with my time. I’ve taken this survey, the entire company knows this is my style, and they are expected to take that into account in interacting with me. Similarly, team members have all taken the survey, and some of them prefer to interact at a slower pace and to have more personal dialogue in each interaction. Just as it is their job to meet me halfway and get to the point in discussions/presentations, it’s my job to meet them halfway and go out of my way to ensure that I am appropriately communicating with them, in their style. I’m sure there are many similar or parallel concepts to DISC that would work for this.

The other side of this point is just general empathy and emotional intelligence. Empathy is not the same as sympathy, and it is not the CEO’s job to give team members what they want or make them feel great. But it is critical to understand the employee — what they want, how they like to be communicated with, why they think the way they do.

Second, knowing what “good” looks like is a key consideration. I’m a young and relatively new CEO. I have seven years of workplace experience. My mental model of “good” from executives is rapidly evolving and is my personal key development goal this year.

I can often instinctively know whether I like a workflow, tactical plan, or policy and whether that fits in with our values. It can take me hours or even weeks to learn enough about the subject to then articulate why I like or don’t like that item. For example, I’ve never worked with a CMO before. To give feedback to a CMO, someone with years or decades more experience than me, is something that I will have to develop over time. I therefore have invested countless hours reading books, hiring coaches and consultants, and working with team members to continually improve on internal articulations of “good” around the company. I find it is exceptionally difficult to give someone feedback around a process that they are using that seems incorrect, when you cannot speak the language of that function fluently.

This is a constantly evolving process that will go on forever. But as we make progress against this and as we define each role in greater and greater detail, avoiding conflict and providing quality feedback becomes easier and easier. I would argue that this is the central role of the CEO function: to pick “good” players and then to coach and develop them to make them better. To do that, you don’t need to be able to do each function, but you need to invest enough time to determine what “good” is in crystal clear detail.

I’ve tried to develop this skillset by personally investing in my own development for countless hours in every conceivable area of business until I feel I get to a critically self-assessed “pass line” whereby I can understand the way a seasoned executive should approach their work, in the context of our business. I plan to double down on getting clearer and clearer in that articulation forever after.

Can you address how to give constructive feedback over email? If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. How do you prevent the email from sounding too critical or harsh?

I don’t think I’ve mastered this personally. I’m sure I write an overly critical email from time to time, and I hear about it when I do. One tactic I’m working on improving is using phrases like, “Please show me how…” or “Can you walk me through this process?” This phrasing allow me to get a better picture into the framework that the individual is using to solve the problem. I find that when team members are employing tactics that do not make sense to me, that A) Often they are right and have great reasons for employing that tactical approach if only I bother to learn about it, or B) We lack a framework or tool that is essential to approaching the problem that we both agree is correct.

An example of a tool is an IRR template. A team member without the ability to accurately gather/estimate costs, project or analyze benefits, and convert this into dollars may be lacking an essential tool to analyze their work product. They may be losing money for the company and have no idea that this is the case. When instructed on how to perform this analysis and asked to use it to analyze their project’s success, they may rapidly transition their approach to a more profitable one.

An example of a framework is the 90/9/1 rule. The 90/9/1 rule suggests that in a forum community (like ours) that 90% of your audience will be “lurkers” who never participate but read and absorb information passively, that 9% of the audience will be “casual participants” who participate on at least some level, and that 1% of your users are the “power users” who create almost all of the posts and content. After a period of wondering about how to tactically approach improving our forum experience for users, the discovery and acceptance of this framework immediately provided us with a much clearer tactical plan to improve the experience for our users, by developing an experience that caters to each of the three user groups.

In your experience, is there a best time to give feedback or critique? Should it be immediately after an incident? Should it be at a different time? Should it be at set intervals? Can you explain what you mean?

I try, on a regular basis, to verbally give this feedback to team members in 1:1 sessions, and informally via internal messaging systems (we use Slack) and email throughout the year. I then formalize this feedback in a performance evaluation. As a business, we have moved from three or four rounds of formal feedback per year to two rounds per year.

The key to a good feedback cadence is that it should be ongoing, and the message contained in formal reviews should not come as a surprise. If my direct reports are surprised by my feedback in their performance review, then I am not doing my job as a manager and leader. Verbal and informal written communication should be clear at all times, during a regular cadence and ad hoc as necessary throughout the year.

How would you define what it is to “be a great boss”? Can you share a story?

I’m still working on this one. I think the answer lies somewhere in creating massive value for users, customers, and society generally; generating high returns for shareholders; and providing growth opportunity and meaningful, engaging work for employees.

I tell every employee who joins that I expect four things for them:

  1. That they understand exactly how they contribute to business success
  2. That they feel they are doing good for society by contributing to our mission and user success
  3. That they feel their opportunity for career advancement is faster here than at other similar companies
  4. That they enjoy coming to work and believe we provide a pleasant environment

There’s a lot more to it than that, but this is my start in answering your question.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could inspire a movement that would bring the most amount of good to the most amount of people, it would be a Financial Independence Retire Early (FIRE) movement. I believe that when high potential individuals are freed from dependence on wage income early in life, that they will go on to creatively and unpredictably have a massive downstream benefit to society by solving world problems, starting businesses, running for office, getting involved in their communities, etc. We dangle this carrot of “drink margaritas on the beach” in front of folks who hate their jobs. This is a delusion. In reality, the folks who build wealth early in life go on to work harder than ever, but on their true passions — and ones that benefit others.

Luckily, I don’t have to inspire this movement. It was going before me, and I got to join for the ride. Our team, BiggerPockets as a business, and I do our part to help people join along for the ride, using real estate as a specific tool on that journey.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The seven “Ps” of success: “Proper prior preparation prevents piss poor performance.” –High School Coach

How can our readers further follow your work online?

You can find me at BiggerPockets.com — just search my name in the search bar or on Google. I have a couple of dozen blog posts, a book called Set for Life, and I interview folks about their journeys with money each week on the BiggerPockets Money Show Podcast with my excellent co-host, Mindy Jensen. I’m also on Instagram at @Scott_Trench.

Thank you for these great insights! We really appreciate the time you spent with this.