If you’ve ever sat in an inbox full of long-winded, unclear, or rambling emails, or had to spend time endlessly scrolling through a discussion on Slack trying to figure out the point, you know how much time is wasted. Poorly written messages create confusion, back-and-forth exchanges, and sometimes, they just get ignored.

Your goal? Write emails and messages that people actually read, understand, and act on—without them having to dig through paragraphs of fluff.

Here’s how. Note that I’ll make this specific to email, but the same concepts apply to all kinds of written messages:

1. Make the Subject Line Work for You

Your subject line is your email’s headline. It should be:

• Clear: “Q2 Budget Approval Needed by Friday”
• Action-Oriented: “Review Required: Marketing Proposal (Need Feedback by Wed)”
• To the Point: If someone can’t tell what your email is about from the subject line, rewrite it.

2. Start With What You Need

People skim emails. If they have to dig for the point, you’ve lost them.

• Bad: “Hope you’re doing well! I wanted to reach out because we’ve been working on the Q2 budget and have some thoughts on the allocations. We’re wondering if you have any time to review it?”
• Better: “Can you approve the Q2 budget by Friday? Details below.”

Put your ask right at the top. If you’re giving information instead of asking for something, state that clearly: “FYI – Updated Timeline for Product Launch (See Below).”

3. Be Specific – What, When, Who?

If you need something, spell it out. “Let me know your thoughts” is useless. What thoughts? By when?
✅ Good: “Please review the attached proposal and send your feedback by EOD Thursday.”
❌ Bad: “Let me know if you have any thoughts on this.”

4. Trim the Recipient List

Before you hit “Send,” ask yourself:

• Who actually needs to see this?
• Will this email add value for them?
• Am I just CC’ing people to cover my ass?

Too many people on an email means no one feels responsible. Keep it tight.

5. Background and Context Goes Last

People don’t need a novel before they know what you’re asking. Get to the point, then provide details for those who need them.

✅ Good:

Subject: Approval Needed: Q2 Budget (Due Friday)

Can you review and approve the Q2 budget by Friday?

• Total spend: $250K (breakdown below)
• Main changes: Increased ad spend, reduced events budget
• See attached: Full breakdown in Excel

Context: We adjusted based on Q1 performance and feedback from Finance. Let me know if you have questions.

This way, they see the key info first, and can scroll for details if they need them.

6. Use Bullets and Bold Key Points

No one wants to read a giant wall of text. Make it scannable:

• Action items: Who needs to do what?
• Deadlines: By when?
• Key takeaways: What do they need to know?

If someone only skims your email, they should still get the point.

7. Should This Even Be an Email?

Before you type, ask yourself:

• Are we brainstorming or discussing strategy? Have a meeting.
• Is this feedback that could get misinterpreted? Talk in person.
• Is this a back-and-forth exchange? Pick up the phone.

A good rule of thumb: If an email goes back and forth more than twice, stop typing and call the person.

Bad Email vs. Good Email

❌ Bad Email (Confusing, Long-Winded, No Clear Ask):

Subject: Quick Question

Hey everyone,

Hope you’re all doing well! I wanted to check in because we’ve been looking at the Q2 budget numbers and there are some changes from last quarter. We think we might need to allocate more to advertising and cut back a bit on events, but we’re not totally sure yet. Also, Finance had some feedback, which I’ve summarized in the document attached. Could you take a look when you get a chance? Let me know what you think.

Thanks!

✅ Good Email (Clear, Concise, Actionable):

Subject: Approval Needed: Q2 Budget (Due Friday)

Hi team,

Can you review and approve the Q2 budget by Friday?

Key changes:

• Ad spend up 10% (based on Q1 performance)
• Events budget down 15% (low ROI last quarter)
• Finance feedback incorporated (see attached)

Next Steps:

• Alex: Approve or request changes by Friday
• Jordan: Adjust numbers in final report after approval

Let me know if you have any concerns.

Thanks,
Matt

Bottom Line

Before you send an email, ask yourself:
✅ Is the subject clear?
✅ Did I get to the point immediately?
✅ Did I include only the people who need to see it?
✅ Is it scannable (bullets, bolding, clear sections)?
✅ Would this be better as a conversation?

Write emails that work for people, not against them. More clarity, less back-and-forth, and no wasted time.

Now go clean up your inbox.

And why the compliment sandwich is BS.

Your job as a leader and manager boils down to three things:

• communicate goals and direction
• set expectations
• give feedback

I’m sure you do a lot of other stuff in the day, and it feels like you’re in meetings back-to-back, but most everything you do should somehow fall into each of these categories. For example, when you’re in a meeting with your executive team or your peers, you’re gathering information on the direction and expectations, and when in meetings with your team or in 1:1s, you’re looking for every opportunity to either clarify direction, set expectations, or give feedback. When you’re devising metrics, you’re setting expectations and building the framework for objective feedback.

I could argue that giving feedback is the most important – as long as YOU are clear on where the team needs to be headed, and what YOU expect, you can manage and orient your team through feedback.

Unfortunately, giving feedback is, in my experience, the skill lacking most in managers and leaders. Many leaders have a “set it and forget it” mentality – they do a good job communicating the vision, but they expect their team to simply go forth and execute. If they do give feedback, they’re saving it for annual reviews.

Great feedback, on the other hand, is:

• specific
• actionable
• timely

Be thoughtful and specific with your feedback. “Good job” is pretty much useless as feedback. Good job at what? What part? Contrast that with “Great job at managing that customer interaction. I really appreciate the way you listened with empathy to their concerns, and addressed each one thoughtfully. That person will be a customer for life.”

Feedback also needs to be actionable – what is it you want them to keep doing or stop doing? For example, “I noticed you got into an argument over email with Joe in sales. Did you notice it escalated quickly, and went back and forth for two days? It’s easy to misunderstand someone over email, and impossible to read cues. From now on, if an email goes back and forth more than once, I’d like you to call the person, or set a meeting to talk about it in person. Typically you’ll resolve things much faster in person.”

And most importantly, feedback needs to be timely. By the time you address your praise or concern in a yearly performance review, we’ve long since forgotten the specifics, or worse, we remember them differently. Or, we’ve learned the lesson and the feedback is now a moot point. If it can’t be addressed in the moment, schedule a call or meeting to discuss the feedback no more than a day later.

Some managers have an attitude that “If I haven’t told you you’re doing something wrong, then you’re doing a good job”. This is also useless, and a wasted opportunity. Good feedback is much more powerful than negative. As human beings, we remember positive reinforcement much more than we do negative feedback. Whenever you see actions and behaviors you want to see more of, point it out.

Which brings me to:

Praise in public, scorn in private.

Whenever you can praise someone in public, do it. Not only will you be reinforcing the right behaviors, but it’s an opportunity to reinforce your expectations with the whole team. For example “You know how I’m always saying we need to be proactive. I want to give Jed some kudos – the minute our supplier was overdue in sending the part, he got straight on the phone with our them. He didn’t wait an extra day or two to see if it would show up, and he didn’t email them hoping for an answer sometime this week. He dealt with it immediately. It turns out our supplier simply forgot. They’re rushing the part overnight and we’ll have it tomorrow so we can stay on schedule”.

On the other hand, no one likes to be dressed down in public. There’s a good chance that the person will be so focused on the the shame. of being called out in front of their peers that they’re really not listening to your feedback, nor is the rest of the team who’s feeling embarrassed or even defensive of their colleague. Save negative feedback for one-to-one meetings when you can discuss it in person, and in more detail.

How do you know if your feedback is being heard and absorbed? Remember that it’s not what you say, it’s what they hear. You can be exceedingly clear, specific, and detailed, but they may not be ready to hear it or may disagree completely. If you have any doubt, ask the person “what did you take away from our conversation?” That gives you the opportunity to hear, in their own words, what they heard, and for you to approach the feedback from a different angle if it didn’t land.

From time to time we have to give particularly tough feedback, which is even more difficult when the person is otherwise a solid performer. For most managers, this is uncomfortable territory and not one we get a lot of practice at. This is where I love the Fierce Conversations model. If you haven’t read it, I highly recommend it. The model goes like this – state your truth, then invite the other person to respond. Here’s an example: “I’m noticing lately that you’re disengaged in meetings. Normally you have a lot to contribute, but these last few weeks I’m seeing you leaning back, rolling your eyes, and not saying much of anything in our meetings. What’s going on?”. And then – listen. Don’t rush to judgement, interrupt, or over-explain. For most people, one of two things are going to happen – either they are going to own their behavior (they may not even realize you’ve noticed), or maybe there’s a reason for it – issues in their personal life, or issues at work that they have a tough time articulating. People are more open to feedback when they feel they’ve been heard, and in either case, you have a much better chance of the feedback landing when it’s a conversation.

Giving feedback doesn’t come naturally to most people, which means we need to practice. So even when (or especially when) it feels uncomfortable, lean in. Don’t worry about your delivery being perfect every time – it won’t be. We’re dealing with human beings. Just keep at it, and it will become more natural over time.

I’ll leave you with one more thing – the advice someone gave you about starting and finishing with a compliment when you have tough feedback to deliver? Toss it out. The compliment sandwich is B.S. By all means, try to balance good feedback with constructive feedback over time, but give one piece of feedback at a time, and make sure it’s specific, actionable, and timely. Giving three pieces of feedback at once in a sandwich is a sure recipe that at least two of them will be ignored, and potentially the third one watered down.

Every leadership book tells you not to delay decisions – that it’s better to make a decision than not, that there’s no perfect decision, and that you probably have most of the information you need now to make a decision.

This is great advice, but what if it’s not clear who is supposed to be making the decision? More often than not, what slows teams down is not an unwillingness to make a decision, but a lack of clarity of how you’ll make the decision, who needs to be involved, and who has the final say.

I’m a big fan of using simple frameworks in companies and teams, because they give everyone a common vocabulary and a shared understanding. One of my favorite frameworks for decision making is DACI. It stands for:

D: Driver – responsible for driving and project-managing the decision process.

A: Approver – is going to have final say in making the decision. In smaller decisions.

C: Contributor(s) – the people who need to be involved in the process, and need to have input.

I: Informed – who needs to be informed of the decision once it’s made?

You can use this framework to clarify both who owns day-to-day decisions, and who owns one-off decisions. Before you dive into a decision, stop the team, and take 5 or 10 minutes to discuss who will be the Driver, the Approver, the Contributors, and who needs to be Informed. When you skip this step, often the team will run in circles with no-one wanting to make the final call, or several people arguing about the decision but getting nowhere.

There’s a caveat to the framework (as there often is) – some decisions are shared. For example, the VP Engineering and VP Product often need to agree on key product features or product direction. It’s ok to have two approvers on really important decisions, but you need to have an escalation path – be crystal clear on what happens when you reach an impasse, how and when to escalate, and who to escalate to to break the tie.

You’ll know that everyone’s in bought into the framework when you hear someone from your team stop the conversation and say “Hey, who’s the D on this?”. In business, clarity is everything, and it’s lack of clarity that will slow you down. Simple, lightweight frameworks can keep you operating at speed as you scale.

Effective Interviewing (or how to REALLY get to know someone in 60 minutes)

Hiring is a funny thing – no where else in life do you choose a partner for a long-term, co-dependent relationship based on an hour-long conversation. Thankfully, there are some proven tactics you can use to get the best possible sense for how a candidate will behave on the job, however they do require some work up-front and some discipline when it comes to the interview.

Preparing for interviews and planning your questions

70% of your success lies in this step. The goal of preparing interview questions ahead of time is to make sure you compare candidates on equal footing, and to help you stay on track in the interview. Have you ever concluded an interview only to realize that you chatted for 10 minutes about their experience, but had a great 20 minute chat about the NHL playoffs?

To start creating a list of interview questions, dig out the job description you wrote for the posting. Using the preliminary job description as a starting point, list the essential job functions – the 6 to 10 tasks, goals, or projects that the new hire will focus on day-to-day. For example, a few essential job functions for a VP of Sales might be:

• Create the yearly sales forecast and break the forecast down into team and individual sales goals
• Build the overall sales strategy for the company
• Create and maintain sales funnel metrics to track overall progress

Again, you should have somewhere between 6 and 10 essential job functions for a given job.

Now, for each essential function, list out the technical skills and work habits required for each of those functions – 1 or 2 for each function. Technical skills are WHAT a candidate needs to know to do the job, while work habits describe HOW they perform in a job. For example, if you were hiring a social media coordinator, and an essential job function is to update the Instagram account daily, a technical skill would be “digital photography” and a work habit would be “self-organizing”. When you’re done, prioritize the list and you should have around 5 skills and 5 habits that are a must for the role. You’re ready to start crafting your questions.

Behavior-based interview questions

Behavior-based interviewing isn’t my idea – rather it’s the central theme of an excellent booked titled “High Impact Hiring”. In my opinion, behavior-based interviewing is the least error prone and most effective interviewing method for technical managers.

Candidates are savvy – they’ve read the books, been to many interviews, and are locked and loaded for the “what is your biggest weakness” questions. The purpose of behavior-based interviewing is to dig into the candidate’s behavior – how do they behave on the job? Past behavior is an indicator of future behavior. The trick is to dig beyond what they want you to hear and find specific examples of how they handled tasks and situations on previous jobs.

From each job function you should have about five technical skills and work habits. For each of these skills and habits, you need to come up with at least two questions (for a total of around 10) that help you determine if this person meets your criteria. Use open-ended questions rather than closed-ended questions.  

Open-ended questions start with: “Give me an example of” or “tell me the story about”. An open-ended question gives the candidate the opportunity to describe behaviors in their own words.

Avoid closed-ended questions such as: “Do you have experience working with Salesforce?” or “Have you ever worked in a fast-paced environment?”. When confronted with a closed-ended question, the candidate will tell you what you want to hear, and nothing more.

Behavior-based interviewing requires that you train the candidate to respond with behavior-based examples. Typically, candidates answer questions with a characteristic, for example, “I’m a good problem solver”. If you dig a little more, they might answer with a general process or testimonial, for example, “In my last job I successfully solved a lot of problems using a problem solving method I learned in school”. Pressed further, they may talk about “what we did at Acme co” (as opposed to “what I did at Acme Co). All of these rely on the candidate’s own view of themselves, or their ability to sell themselves – both completely useless to you. None of these responses tell you “does this person really know what they say they know”.

What you need is a behavior-based description – a story recalling a single event with considerable detail what they did given a certain problem or situation. You can train the candidate by asking them open-ended questions built around a handy acronym – STAR: Situation or Task, Action and Result. For example: “Tell me about a specific time when you used your problem solving skills. Tell me about the Situation or Task, what Action you took, and what the Result was.” Keep digging – ask for more detail and rephrase the question until you find out what the real action and result was.

Beyond behavior-based interviewing, here are a few other tips we’ve picked up to getting the most out of every interview:  

Use silence to your advantage. Silence is uncomfortable, but fight the urge to  help the candidate along and give them hints about what you’d like to hear; let them know they have time to think and let them formulate the answer.

Interrupt to maintain control: Mom always taught you that interrupting is rude, but in an interview, you have to interrupt from time to time to make sure you get through the full set of questions. If you run out of time with seven questions unanswered, you will have no way of comparing this candidate on an equal, objective footing.

Never answer your own questions: It’s tempting sometimes, especially if the candidate is keen, to give hints or help answer questions. Let the candidate sweat it out if they don’t know the answer. Give them a reasonable amount of time (a minute) to answer and move on to the next question. If they don’t know the answer, it’s not your responsibility to teach them either.

Pressure cooker questions: I like to introduce a question or two that is a little uncomfortable to answer, but will give me some insight into how they work with others. One of my favorites is “what did you and your manager disagree on most often?”. The key is to not let them off the hook. Their first answer will almost always be “nothing, we got along great”, to which your follow up should be “Of course, but there has to be something on which you didn’t see eye to eye”. Their answer can give you interesting insights into how they manage conflict.

The Impossible Question: The Impossible Question is something I borrowed from Microsoft and Joel Spolsky. It’s fallen a little out of favor lately, but I still like it as a way of judging how open-minded someone is, and how they react to challenges. It’s a question the candidate will have no hope of answering correctly, which gives you a strong indication of how they will react to tough problems. An example of an impossible question would be, “how many gas stations are there in Philidelphia?” or “how would you move the Washington Monument to Los Angeles?”  A smart candidate will realize you’re not quizzing them on their knowledge, and enthusiastically jump into trying to solve it – these are the people I look for. Others will look at you like you’re crazy, and will need a lot of prompting. An important thing to note is that The Impossible Question is NOT a puzzle or a brainteaser. Brainteasers tell you nothing except whether or not the candidate has heard the puzzle in the past.

Leave time for their questions: One of the most insightful parts of an interview are when you turn it over to the candidate and say “What would you like to know about working here? Ask me anything”. What they ask (and don’t ask) tells you a lot about their values, and about how well they prepared for the interview.

In the next (and final) installment on hiring, I’ll dig into how to decide among candidates, how (and why) to do reference checks, and making the offer. Stay tuned!

Screening resumes

If you’re lucky, you’ll receive lots of eligible resumes, but everyone dreads the drudgery of screening resumes. Hopefully, your self-screening tactics have whittled the number of resumes down to dozens, rather than over a hundred, but still, that’s dozens of resumes to read and evaluate. Here are a few tips to make the process a little less painful.

When you’re screening resumes, don’t try to jump straight to a Yes or No on the first pass. You’ll find yourself reading, and re-reading resumes and either throwing out too many or including too many to interview. It’s really hard to tell if someone’s a fit based on the resume. At this stage, you’re just trying to stack-rank them so that you can prioritize your interviews. Instead of a Yes/No, grade them from AA to D:

• AA: Wow. Looks like exactly the person you were looking for. E.g., has exactly the right amount of relevant industry experience (you’ll probably only have a few of these)
• A: Relevant experience, at the right level of responsibility; no red flags
• B: Some experience, but maybe a little more junior than you were looking for or not quite the scope of experience
• C: Has some of the right experience, but there are some red flags, like jumping from job to job, resume typos
• D:  Not enough experience, the wrong kind of experience, or a poorly written resume

If you don’t have a resume-tracking tool or hiring portal, an easy way to manage the process and keep them organized is to put all the resumes in a folder, and rename the file leading with your ranking. For example, “B_JohnDoeResume”. You can add a suffix to keep track of where they are in the process, e.g. “B_JohnDoeResume_screened”.

Trust your gut. Don’t overthink it, or you’ll be at it for days. Only go back and do a second pass if you find yourself putting everyone in the B category, or if you end up with more than a few AAs and As.
Hopefully you have 2-3 AAs, and something like 5-7 As. Set up a screening interview with these candidates first. If you eliminate too many in the screening process, you can always move on to the more promising B candidates, but chances are your final candidate is somewhere in this initial list.

The screening interview

You can save yourself a considerable amount of time by screening candidates by phone before conducting face-to-face interviews. There’s nothing worse than spending an hour or more in an in-person interview only to find out they can’t move to your location, don’t really have the experience they are touting, or aren’t interested in working on your product.  Phone interviews should be no more than 20 minutes, and should mostly be focused on verifying the facts on the resume – current position, current responsibilities, basic contact information, location preferences, willingness to relocate, and salary expectations. Take a few minutes to ask them about their current role and responsibilities. There’s no need to go too deep here, rather, try to get a sense of whether they are embellishing on their resume, or if they do really have the level of responsibility they are stating in the resume.

The screening interview also gives you the opportunity to gauge their communication skills, both in the process of setting up the phone call, and the call itself. How quickly did they respond to your email requesting a phone call? Was their response succinct and well written?

Incorporate one question that helps you determine if they have the single most important technical skill for the role. For example, if you’re hiring software developers, it might be a question to determine if they really understand OO programming. If you’re hiring automotive technicians, it might be a question about how they’d diagnose a tricky non-start condition on a specific make/model.

Next week we’re going to dive into the interview – how to prepare questions, how to really dig if you’re not getting the right level of detail from a candidate, and dos & don’ts for the interview itself.

As I write this, we’re in what we hope to be the tail end of the pandemic. Businesses are reopening and hiring (or if you’re in certain industries like Powersports, you’re having a record year). Several of my clients have asked me to either help them hire for a key position, or to help coach and train their team on effective interviewing and hiring. Over the years, and over countless hires (and even more interviews), I’ve tried to refine my hiring process to make it more repeatable and less error prone. Hopefully, you too are hiring, and this process can help you make your next hire a little easier. Here’s Part One – laying the groundwork and creating your job posting.

The groundwork – writing the job description and the posting

The key to successful hiring starts with a solid job description. Not only will it help you write a posting that attracts the right candidates, but it will help you build your interview questions. The job description needs to include: 

• Title
• Primary tasks and duties
• Responsibilities and authority
• Reporting relationships (who will their manager be?)
• Qualifications and characteristics (what skills and personality traits do you need for this role?)
• Desired experience
• Organization level (Jr., Intermediate, Manager?)
• Education requirements
• Salary range

These bullet points give you all the information you need to write your job posting, but describing the job is table stakes. Despite what the media may tell you, qualified talent is scarce. Your job posting needs to stand out. Don’t be dry. Let the personality of your company come through. Tell applicants why you’re a great place to work, and what to expect from the culture.

Let your candidates help you screen the resumes

Screening resumes is a drag. With any luck, you’ll get dozens or hundreds of applicants, and trying to whittle that down to 5 or 6 people you want to interview can be really time consuming.  Make this more manageable by having the candidates do this for you.

Whenever I post a job, I try to devise a way to separate the people who are genuinely interested from the people who are just carpet-bombing companies with their resumes in hopes of a hit. In the job posting, I include – in plain sight – detailed instructions of how to apply for the job. For example, I might say that we only accept applications through email, and that we don’t want a separate cover letter –  instead, write us an email, and we’ll only accept resumes in PDF or Word format. Anyone who doesn’t follow the instructions, I immediately delete. It might sound counterintuitive,  but that self-eliminates the bottom half of the applicants. My theory is, if you can’t follow simple instructions, or you can’t take the time to read the whole posting, I don’t want to work with you. From time to time, to test my theory, I’ll interview a candidate who has a decent resume but didn’t follow the instructions. In every case, the interview was a waste of time. The candidate either lacked attention to detail, had a sense of entitlement, or had a massive ego.

I’ll also make a second ask to help me narrow the field down further. If I’m hiring for a specific skill-set, say a designer or a writer, I’ll ask for samples or a portfolio. In other roles, I’ll simply ask them to write an email describing why they think they are a fit for the role, and why they are passionate about the industry. Another 10% of  applicants won’t follow the instructions, which I immediately delete. For another 10%, their portfolio or samples won’t be up to par, or their email will be poorly written or simply sloppy (punctuation anyone?). Before even starting to screen resumes, you’ve already eliminated 70% of the work.

Where to post

Where you post your job depends on the type of skills you’re looking for. Overall, I find LinkedIn works best for knowledge-based roles and management positions, especially if you pay to boost the posting and broadcast the job to your LinkedIn network. Many of my clients have had good luck with Indeed, and for technician roles or entry-level positions, you can’t beat Craigslist. Make sure you post the job to your company website, and encourage your staff to share the job posting to their social media networks. Often the best candidates come from staff referrals.

In the next article, I’ll show you how to make it easier to screen and track resumes, and how the screening interview can save you a ton of time in the interview process.