The recruiting process is mystifying for most. The internet is full of guides on parts of the interview process that matter the least, such as what exact questions to ask (“Google interview questions,” Leetcode, etc.). The crucial parts of the recruiting process, when you create a lasting connection between a candidate, the company, and the hiring manager, are overlooked. The candidate closing step, in particular, is daunting for first-time hiring managers and founders.

Suppose you found the right candidate and spent hours of your team’s time interviewing and arguing with other leaders about offer details; you owe it to yourself and the business to give yourself the best chances of closing them. To close the candidate, you need to get the candidate excited and willing to join your team. It won’t be a small task. Why? Candidates may have competing offers. Their current company may try to counter your offer in the future. Think about it: the company they’re currently working at has the candidate’s ears for the next few weeks. Imagine how much fear, uncertainty, and doubt they can create (and trust me, they will). A good candidate closing conversation is the best defense against the hesitation and questions that will build in the days it takes for candidates to decide.

There’s no secret to closing a candidate, but there’s a way to do it right. Let’s get started. If you want to skip the preparation, just go to the “The conversation” section.

At the heart of a good candidate closing, you want to create a lasting excitement that connects the candidate, the company they are considering working for, and you, their hiring manager. Alternatively, if you think the connection is missing, your role is to establish that it’s not a good fit.

[Note:]{.underline} Some closing conversations result in you or the candidate deciding there’s no good mutual fit. Trust me, that’s a way better outcome than hiring this candidate.

Let’s start by defining your responsibilities as a hiring manager. The hiring manager should…

• Remain honest and direct. Lying during the closing process will only get you in trouble later. Some hiring managers think closing is a “sale” where you’re supposed to embellish the situation to get a candidate to join. When the candidates realize they’ve been fooled, they will leave; that outcome is awful for your business.

• Create clarity and safety. Accepting or refusing an offer is scary. No one likes to say no, and candidates will have to say no to something in the future—this offer, another opportunity, or their current job.

• Provide a tight closing experience, with deadlines and clear steps. A candidate’s excitement is finite—candidates are never as excited as when they first receive their offer. It’s downhill from there. Managing time is managing expectations.

• Give an accurate view of the opportunities and challenges that are in it for them. People love to dream about a great offer, but no one wants a softball offer with no challenge ahead.

Before any closing conversation, the hiring manager should…

1. Have the offer details memorized and easily accessible. No reasonable questions should be left unanswered. For a tight closing, the hiring manager should be able to answer candidates’ questions on the spot. Any delay means that the candidate will need extra time to decide.

2. Review and summarize the interview notes from the interview circuit. The candidate needs an honest review of their performance, highlighting the good and the bad aspects of their interview performance.

3. Asked the candidate if they were ready to receive an offer ahead of the closing call. Hiring managers should be able to explain what it means to be prepared to accept an offer. Typically, a good rule of thumb is 5-7 days to say yes or no from the day the offer is delivered. Hiring managers should not accept a day beyond the deadline. It seems like a strict rule, but excitement is limited on both sides. We’re excited about getting them on board; we expect excitement in return. Over the last eight years, I haven’t seen a single candidate asking for more time that I ended up closing. If the candidate mentions that they can’t commit to that timeline, no problem. Wait with the offer in hand until they say they are ready. They risk having the offer going to someone else, but we can’t hold the line for them.

Now that I’ve done that, it’s time to give the offer and do the closing conversation. I usually book 45 minutes, but it can be done in 30 minutes. Call or meet the candidate; don’t do it by email. You need to build a connection. There is no shortcut.

The conversation

Below is a timeline for the closing conversation.

1. Part 1 — the SELL (10-15mins) - I start by sharing the feedback from each interviewer. I always highlight the votes of confidence from specific individuals on the team, using their names and quotes. My role as a hiring manager is to provide an accurate picture of the candidate’s strengths and, more importantly, where the team plans to use these strengths. I ask candidates for feedback and make it interactive so it’s a conversation and not a boring monologue.

2. Part 2 — the “UNSELL” (10-15 min) - I have seen too many hiring managers skip that part. Let me be clear: it’s the most critical part of the closing and a key part of why people will join your business. Candidates expect to be challenged and grow in the position they’re joining. During the UNSELL, this is your chance to pinpoint precisely where you expect them to grow by showing them where they fell short in the interview. The aim is not to hurt their ego but instead show that, as your hiring manager, you started to build a path to grow them professionally as a manager. The more specific you are, the more. Ask for feedback here, too. Is it something that they’ve noticed about themselves? Did they struggle with this in the past, etc…

3. Part 3 — Offer details (5 min) - I spend 2-3 minutes giving the candidate high-level information about their offers. The most useful is a “startup comp 101” speech on stock and options and the company’s compensation philosophy. For example, if you use the 75th percentile for similar roles in the industry, tell them. Make sure to answer any clarifying questions. People get weird with money, so I pause to let them ask questions during a five-second silence. This is also the time to give the deadline for deciding. If they ask for more time, ask them why they believe it’s necessary. It’s powerful to remind them that you asked if they were ready to accept the offer beforehand, so you’re surprised by the change.

4. Part 4—Feedback (5 min) - “Is that an offer you can see yourself saying yes to?” “Would you be ready to give a verbal yes, or is it too early?” “Is there anything pressing we should address?” I wrap up the interview with these questions. I don’t want to push too hard, but getting a candidate’s live feedback can be very helpful in gauging how engaged they are. I want to prime them to react on the spot and tell me what I can expect ahead.

5. Part 5— Wrap up (1 min) - Tell them what’s ahead, that payroll/HR will send them offer details, and that you will keep in touch. Candidates are my priority until the due date, and they can call or email me anytime.

Once you’ve hung up, have whoever is in charge of payroll or human resources email the candidate with all the offer details. I encourage all the interviewers to send a thoughtful message to the candidate once the offer has been sent. This will make candidates feel less lonely and more connected.

As a hiring manager, I connect once a day with the candidates via text or email until they say yes or no to the offer. Sending them articles about the business, news, and social media news connected to the company will keep them connected and show that you care.

On the day the offer expires, I meet for a last time and, if they are still undecided, repeat gently that the deadline is firm, but a deadline is a deadline, and it can’t be renegotiated at the last second. Luckily, if you’ve followed the steps above, that will not happen as a surprise.

First, let’s define what a Product Outcome is. A Product Outcome is an actionable behavior change that will lead to business results. Now, how do you figure out the right Product Outcome?

Start simple.

Before you’ve had multiple customer conversations, don’t spend time trying to guess what the market needs. At best, it’ll just be guesswork. At worst, it will end up as confirmation bias that will be difficult to eliminate later.

However, if you already have customer conversations recorded, you may be able to find behaviors you want to target from the opportunities you’ve listed.

Start with a business objective lens.

The behaviors you want to target are the ones that will lead to business results, meaning they must align with your business needs. For product teams, “business needs” means that users/customers will use one or multiple features you have in mind.

For example, if you want to sell a new product to customers, start with “Users trust/use product X.”

Such product outcomes will need to be refined, and product teams will be required to stay aware that the feature/product may, in fact, not work. But this kind of product outcome is helpful to run the first few customer interviews.

Evolve it over time.

The Product Outcome is important, but it is not sacred. Like any first attempt, the first Product Outcome won’t be amazing.

Change your Product Outcome as you debrief your product interviews, review opportunities, or evolve your prototypes.

Small but ambitious

A Product Outcome should put you one step towards a product that customer love and use and a viable business model.

Typically, Product Outcomes need to be fixed in two ways.

1. They are too generic. The lack of focus it will create when reviewing opportunities and solutions will invite delays in release and a bloated experience. Your first customers will have to deal with an overly complicated, unfinished first attempt—a recipe for disaster.

2. They are too specific. This is the other end of the spectrum where you narrowed the Product Opportunity so much that the opportunities you will find in customer interviews work for such a thin slice of customers that the product will never create a viable business. Note: This is an easier problem to fix than a too generic product because the signs will be obvious.

There is no secret formula to write a perfect Product Outcome. The right Product Outcome sits somewhere between generic and specific and depends on many factors like your business size, industry, maturity of the market. A product manager’s intuition and experience will play a large part in how quickly they unearth a good product outcome.

If you’re a founder or product manager looking to build products that customers will use and love, you know how important it is to think about Product Outcomes. But instead of trying to approach it through perfection right away, see it as another step that you review every week or month to make sure you’re on the right track.

Creating a winning attitude starts with you. Show a willingness to work hard towards the objectives set by the team and company. Make sure that your contributions towards the goals are clear.

As a leader, you must believe that the objectives are worth it. You shouldn’t question the mission and goals of the company/team in front of your team. If you have doubts, how do you expect people working for you to follow?

Have a positive attitude towards the mission and goals. Make sense of the mission and repeat how important you believe it is. Show one or multiple paths to hit the goals and emphasize how it can be done instead of delving into how it could fail.

You must set goals and standards that your team has a chance of hitting. If the goals are too high, the team will be set for failure; the team will know it can’t win and won’t try.

Repeat the goals in front of the team often. Have a public scoreboard showcasing the progress towards that goal. The team should know the skills and next move required to hit the next milestone to get to the goal.

If possible, create healthy competition between teams to reach the objective. For example, if multiple paths exist to achieve the goals that multiple teams can contribute to, set up a challenge for whoever helps the most between the two groups.

Teamwork is crucial, but make sure to acknowledge individuals as well. Congratulate team members when they go out of their way to help achieve goals. Reward high performance as soon as you notice. Other leaders can help you point out high performance if you ask them to point out when one of your team members does something.

Work to get your team publicly recognized by the greater organization for its contribution. All hands, board meetings, and public channels are great places to highlight what your team has done.

Allow people to showcase their skills outside of the regular cadence of your organization. Hackdays, brownbags allow employees to excel in skills they learned in a different context.

Finally, create pride in your organization and team's “story.” Every company has a story of humble and scrappy beginnings. Use these stories to contrast the past with today; a powerful story is a force multiplier in creating a winning attitude in people. There’s pride and energy in seeing the work required to get to where we are.

Startups have the advantage of a short history; make use of it.

1. Listening

2. Information Processing

3. Information Sharing

4. Self-starting

5. Plan & Strategize

6. Manage your time

7. Efficient Meetings

8. Set Standards

9. Delegation

10. Review standards

11. Maintain High Performing Team

12. Provide Feedback

13. Reward Individuals

14. Deal with low performers

15. Deal with troublemakers

16. Counsel

17. Improve Performance

18. Provide feedback to a team

19. Reward high-performing teams

20. Deal with low-performing teams

21. Motivate

22. Prepare for tough times

23. Handle stress & unforeseen issues

24. Create a winning attitude

25. Supervise

26. Ask Questions

Departures in startups feel personal and scary. Employees will ask me whether the business will be affected or if *BAD THING* is happening, but they’re oblivious. After seeing dozens of departures over my tenure as a founder, I’ll share a few thoughts on dealing with them.

Departures are losses, creating real grief that most coworkers must work through. If the startup is smaller than 150 people, Dunbar’s number, every employee will have a personal connection with the person leaving. Unsurprisingly, people go through something like the five stages of grief as they process the news.

At some point, most people will ask leaders for answers during one of the stages. As a leader, I often remain publicly silent on the topic. For good reasons, building a habit of addressing every departure is not useful and fraught with privacy concerns.

However, I understand that a departure is a new and disturbing event for some, so it’s always good to remind yourself of a few principles.

(1) People are the most important element in a company’s success. Do not dismiss this statement as a tired trope. Nothing, and I mean nothing, would happen at a startup if we didn’t have talented people to move things forward. 

(2) All leaders care and feel sad when people go. We care more about losing the person and the personal connection we’ve created than the “resource.” Don’t mistake silence for lack of emotions/care.

(3) People leaving a startup is normal and even healthy. Each one of us has personal goals and priorities. We hope these priorities align with Truework’s and my team’s. However, they may diverge over time. Life is unpredictable, and so is tenure at a company. 

With one, two, three, or more departures, the brain goes into overdrive to decipher what it means for you or the company. Often, it’s a red herring; the brain loves to see patterns, even when there’s nothing.

Instead of worrying, I encourage everyone to see people’s decisions as individual paths rather than drawing premature conclusions. Choose to celebrate their contributions for each departure. Ask yourself how we can continue their work and make the company more successful. One day you’ll be the one that left. Do you want to leave a trail of rumors and disgruntled people behind?

Looking back, I gave no credit to the power of the mind and resets. True, January 1^st^ is just an arbitrary day. True, it will require hundreds of hours of practice to transform a resolution into reality. But, that date gives many a chance to find a footing to start a real change.

So, I don’t ignore new year’s resolutions anymore. The sarcastic comments in my head after someone shares their desire for the year are gone. If the first of January gives you special powers to turn down a bad habit or a friend’s invitation to go to a bar instead of working out, great!

Short list of resolutions for 2023

First, I want to improve clarity. After settling into my leadership role, clarity is now the limiting factor to how much and powerfully I can influence, energize and motivate people to work together. My mind revels in complexities. Selfishly, I want to invite people into that world by waterboarding them with as much information as I can. That behavior doesn’t consider the complexity that people wrestle with in their own life/work. My lack of clarity compounds with their issues, making it difficult for them to take quick and decision actions.

Second, continue reading. I’ve picked up my reading pace, but there are more unread than read books in my library. Science-Fiction is one of my favorite genres, and I’d like to finish more in 2023 instead of focusing exclusively on “utilitarian” books (it doesn’t mean they’re bad).

Third, continue musical explorations. Creating music is such a fun activity. I’ve picked up bass guitar recently, and it’s been a blast. I want to do more (see Milestones) and learn to write music. On the physical level, I want to continue pushing myself. With the pandemic well and truly over, being active is simultaneously easier and harder than before during the pandemic. Easier because more activities are open and in full swing. Harder because face time with coworkers is key to success, but it means more constraints in where to go (again, see Milestones). And I need to lose 7-10lbs.

Milestones

1. Play at least one open mic. I’m terrified of playing in front of a crowd where I can’t excuse myself for not sounding great. That feels like a scary but achievable milestone for music.

2. Physical challenge milestones – Climb Mt Shasta. We got turned by the weather. This year will be the one! Run at least one marathon. I’m not much of a long-distance running competitor, but I finished with ease the half, and I’m ready to get to the next level.

I have work milestones, but they’re better shared later in the year.

Stop doing

I rarely peruse the typical social media websites. However, I spend too long on some founder/engineering-focused websites.

My time would be better spent doing anything else, even doing nothing than this. I barely learn anything new on these websites, and their negative tone and depressing takes are too high of a price to pay for the scant teachings.

The failure of Engineering and Design teams to understand product strategy is too often considered acceptable or, worse, expected. If you’ve heard “Engineers don’t want to hear about customers,” you’ve been on that kind of team.

Leaders should be alarmed when this situation arises, yet it’s rarely identified as an issue.

The signs are not obvious. Sometimes it’s seen in product launches with no adoption as customers find little value in the new product. It also shows up in slowly delivered features, low-quality results, and a disengaged team passively expecting work orders as JIRA tickets.

The work motion becomes exclusively top-down - leadership hands down product ideas, product managers write a product spec in isolation, and the engineering team codes it. Product motion is a slow, painful waterfall.

Of course, this is not how the best products are built or how a team becomes empowered and engaged. To connect day-to-day activities and long-term strategy, Engineers, Designers, and Product Managers must think about business and understand customers.

Connecting business, customers, and product work is more straightforward in some industries than others. B2C companies have an advantage, as product teams are more likely to use the product, thus connecting the dots. Product leaders must go the extra mile in B2B businesses. Product teams are more than capable of understanding customers if they are given the tools and information required. This task is one the product team needs to tackle directly and continuously.

Before diving into how to share business context, I recommend testing where the team stands by running the JIRA Test exercise. The exercise aims to see if team members can tie the team’s sprint work to the company's mission and metrics.

How to run the exercise

You can use stickies or a tool like LucidChart. One advantage of tools like LucidChart is that they can pull JIRA tickets dynamically.

First, get the team together and randomly pick 10-15 recently resolved/completed JIRA tickets.

For each ticket, ask team members if they can

• Identify what opportunities are tied to this ticket.

• Name the bets the team had placed on this work.

• List leading metrics we hope to influence with that work.

• Connect one or two company-/team- key results or metrics the ticket impacted.

Once the exercise is complete, recap with the team. Be honest with them; the failure to answer these questions is not on them. In fact, it’s on the product team and leaders!

If your team did great, they could tie work to opportunities and bets and finally talk about how they contribute to company objectives; amazing! You’re one of the few product teams that have managed to empower your Engineers. On the contrary, if the team sees their work completely orphaned from business objectives, you have work to do!

People’s desire to understand extends far. The need to find meaning in work is a basic human need. So powerful is that need that studies show that employees would cut their salaries to get more meaningful work.

I often hear the excuse that the startup is not doing something big enough for people to care. That’s a cop-out; there’s no need to build rockets to Mars for people to feel a sense of purpose. Almost anyone can get excited about something when they understand the “why.”

The Product Team is here to provide a shared context for the team. When it’s not a company mandate, the whole company suffers. Productivity is low; attrition is high.

A five-year journey and, today, a series C announcement.

I wanted to take a few moments to reflect on what it takes to get to Series C. I’ll try to avoid platitudes. If you notice a couple of them, know they’re caused by a limitation in my writing abilities, not my feelings, that doom me to write them.

A startup is not a non-stop “it’s awesome!” experience. I’m sure that, at multiple points in this year, you’ve been frustrated, irritated, or disappointed. Maybe a project you cared about fell off the roadmap because we lacked the resources. Perhaps an idea you loved didn’t stand the test of time, customers didn’t like it. I’m sure of that because I experience this frustration too. Temporary frustration is the price we must pay when ambition, limitations, and an uncertain future are mixed together.

But there’s another prize, delight! The same unknowable future also holds a bright future - Series C, a large customer that changes the course of the company and makes us proud that we’ve toiled and, against all odds, succeeded.

I sincerely wish you take the time today to feel proud. Proud of how far you’ve helped push the company and proud to know how few make it to this point.

For tomorrow you may feel frustrated, but today you should feel happy!

Cheers,

Have you ever been in the presence of somebody with whom every interaction is stressful? You must carefully weight every move next to them. If you don’t, they’ll get offended, explode in fits of rage, or become passive aggressive. Now, reverse the roles, imagine you’re that difficult person.

Difficult leaders cut themselves from the bedrock of good decision making – unfiltered truth. Who, in their right mind, wants to share difficult but critical information with them?

It’s difficult to recognize yourself as a toxic leader. You truly believe that you’re doing the right thing.

Here are some signs you may be a toxic leader.

• Are you quick to reply?

• Do you jump in the middle of discussions and witness health debates suddenly coming to a halt?

• Are you easily offended?

• Are you inflexible?

• Do you feel better than everyone else?

• Do you feel invested in a great mission and the end justifies the means?

Often leaders believe that being difficult is going to prevent setting low expectations on a team. They believe only the relational with other people will suffer from their behavior. That’s incorrect; something far more valuable will get lost. Poison will seep into the well of unfiltered truths. In organization with toxic leaders, people work towards minimizing blowbacks instead of optimizing for truth.

Be easy to deal with.

The most straightforward path to weight loss is sustained calorie deficit. A calorie deficit means ingesting slightly fewer calories than your body needs. For men of my size and activity level, a two hundred calories deficit per day amounts to one pound lost per week. The math is easy, but success hinges on having the willpower for long enough and a way to track calories. Two hundred calories is a small amount of food. MyFitnessPal is the best app to track calorie intake. You input the food you had during the day in the application; it gives you the number of calories. You stop eating once you've reached the calorie target, and voila, you're on your way to losing weight!

The input of food day after day is tedious, but it works well enough. Additionally, the application shows all kinds of statistics that made the geek in me happy. I knew how much sodium, calcium, and other nutrients I was getting daily. After a few weeks, I could see the results on the scale. My weight was finally going down!

Then, things turned interesting.

Without me realizing it, calorie counting turned slowly into an obsession. I wanted, no, I needed to enter every meal into the app and count every macronutrient. I refused to eat items not listed in the application. I felt depressed and anxious if my calorie intake was 50 calories above target for a day. I worried about every drink, every bite of food.

In truth, I had stopped calorie counting to lower my weight; calorie and macronutrient counting was now my goal. Months went by before I stopped using MyFitnessPal, far after I had reached my weight goal.

But this is not a story about my weight loss and calorie counting. Remember how I said things were rough for us at Truework in that period? Compared to making the startup successful or the act of losing weight, inputting food day after day was straightforward and more predictable. I would get my dopamine hit when I hit my goal.

Counting macros and calories was complicated but tractable complexity. Calorie counting was a relief in times of stress, surrounded by complex projects!

This pattern is common across people and organizations. Products are hard to build, and products rarely succeed in the market. Managing management is stressful. Business outcomes are challenging to drive and take months or quarters to become a materialize.

Confronted with that level of complexity, organizations naturally gravitate towards tractable complexity. They trade the "hard stuff" for tasks they control, even when these tasks loosely relate to the original goal.

• Making sure the organization is secure? That's hard, but we can update dependencies at the slightest hint of a security notice.

• Launching a new product? There's no guarantee this product will be successful or that customers will love it. Instead, we can focus on refactoring the old code and maybe changing the database before launching the product.

• Writing a new post on this blog? That’s a lot of work. Better to look for a new note taking tool.

We all want to avoid dealing with tough challenges and prefer tackling small items. Who doesn't like victories?

I don't claim that breaking down large tasks into subtasks is a bad idea. It's helpful and powerful to give your team a sense of moving forward. However, as a leader, you must ensure that you keep yourself and your team honest about what challenging problems they must focus on.