Your Career Compass

Photo by Bakr Magrabi


Promotions, project assignments, and pushback in meetings all come with trade-offs. Without a clear set of core values you’re just guessing which choice is right. With them you have a built-in compass that points you in the right direction even when the map is unclear.

What Are Your Core Values?

They are the deeply held beliefs that shape your decisions and actions. They’re the “why” behind your “what.” At work, they are the difference between wise choices and the ones you regret six months later. If you don’t know what your core values are, here is a list from Brene Brown (thank you!) to help you define them. After looking at the list:

  • Choose 10–15 values that resonate with you. Take your time but don’t overthink it
  • Whittle those down to 3–5. This is hard. Focus on what really drives you
  • Check your behavior against your list. This is where it gets uncomfortable: notice what you do, not just what you say. Values are only real if your actions reflect them. For example, if you say honesty is a core value but you leave inconvenient details out of a client report because it makes your team look better, then you may not be as committed to honesty as you thought. That’s not to shame you. It’s to help you notice when your behavior doesn’t match your stated values. The gap is revealing

Why Core Values Matter at Work

Leaders face this all the time: two options, both high stakes, both with trade-offs. Core values act as a filter. They help you set aside other people’s expectations so you can make decisions that align with who you are. For example, in a team meeting your manager proposes a project timeline you know is unrealistic. If one of your core values is integrity, that value pushes you to speak up even if it’s uncomfortable. If your top value is loyalty, you may frame your concerns differently, focusing on supporting the team while raising the issue.

Use Core Values to Guide Your Career

Short-term example: Your manager asks you to join a new project that would be great for your visibility but would require late nights for the next three weeks. If one of your values is balance, you may decide to pass or negotiate a more sustainable schedule. If your top value is growth, you may accept and plan for recovery time afterward.

Long-term example: You’re considering a job offer from a company with a reputation for high turnover and aggressive targets. If stability is a top value, you may decline. If innovation is a top value, you may decide the fast pace aligns with what you want.

In both cases, your values act like a GPS. You still choose the route, but they keep you pointed toward your destination.

How to Apply Your Core Values Right Now

  • Write them down and keep them visible: Put them on a sticky note on your laptop. Take a photo of them and use it as the wallpaper on your phone
  • Define 2–3 behaviors for each value: This makes them measurable and realistic
  • Run decisions through your values filter: When faced with a choice, ask: “Which option best aligns with my values?”
  • Use them in conversations: If you decline an opportunity, frame it around your values. For example: “I want to make sure I can deliver quality work, so I’m concerned about the current timeline.”
  • Revisit them quarterly: Your values may stay the same, but your behaviors may need updated as your career progresses

How do you use your core values to make wise career choices? Please share in the comments.

Are You Ready for It?

Photo by Andrea Piacquadio


It’s promotion season! The time of year when titles shift, responsibilities grow, and opportunities open up. Whether your company follows a formal review process or leaves advancement up to individual managers, one thing is clear. You aren’t handed a promotion. You have to be ready and strategic.

Close Gaps

Before you ask for a promotion look up the job description for the role you want even if it’s not currently posted. What skills, certifications, or leadership abilities does it mention that your current role doesn’t require? Skill gaps aren’t deal breakers. But if they’re visible and unaddressed, they’re easy reasons to pass you over. Your good work does not speak for itself. Promotions go to people who proactively show they’re already doing some of what the next-level job demands. For example, if the job requires strategic planning, and you’re currently in a tactical role, think back to when you helped your team decide on quarterly goals or you made a case for prioritizing a project. Document that and be specific.

Highlight Impact

Instead of listing your tasks clearly state the outcomes your work produced. “Created reports,” is fine, but what happened as a result? You can say, “Increased reporting efficiency by 30% by restructuring our monthly deliverables.” When pitching yourself for a promotion, share examples of projects that had measurable impact. Then tie them directly to the role you want. For example, “Last quarter, I led a small team to implement a new client feedback loop. The experience taught me how to adapt communication styles across departments. That skill is required in the new role on a daily basis.”

Be Clear

Vague descriptions make it harder for others to see you in a bigger role. Swap out generic phrases with specific, transferable skills. Instead of “Ran meetings” say, “Facilitated weekly team syncs, keeping cross-functional partners aligned and on track.” Your goal is to make it easy for your manager to visualize you in the new position. Not just because you’re ready, but because you’ve already started acting like you’re in it.

Build Relationships

If no one in leadership knows your work, they can’t advocate for you when decisions are made. Be visible in the right ways: Speak up in meetings with thoughtful questions or insights. Offer to present team wins or project outcomes. Ask for feedback. Not just from your manager, but also from peers or other leaders you’ve worked with. If your manager knows the promotion is a stretch role, don’t shy away from acknowledging it. Say something like: “I may not be the most obvious candidate on paper, but I’ve been working intentionally to grow in these areas, and I believe I can bring real value to the team.”

Ask Professionally

Once you’ve done your prep, set up a meeting with your manager. This is not a casual hallway conversation. Frame it as a career development check-in. Come prepared with: A list of accomplishments tied to the new role. Evidence you’ve closed (or are closing) any skill gaps. A clear statement of your interest in the position. You are not bragging. You are owning your progress and signaling your readiness. You can say, “I’ve taken on more responsibility over the past year, and I’ve had the chance to lead several initiatives that improved team efficiency. I’ve reviewed the expectations for the position, and I believe I’m ready. I’d like to talk about what it would take to be considered.”

How do you clearly demonstrate the value you bring? Please share in the comments.

Pitching Change

Photo by Christina Morillo

You know you need presentation skills for giving a speech. But if you work with other people, you’re presenting all the time. In a Slack message. On a Zoom call. In a 15-minute check-in. Anytime you share an idea, pitch a change, or walk someone through your work, you’re presenting. And how well you do that matters. A lot.

The ability to present your ideas clearly and confidently is a soft skill that affects how you’re perceived, how well you get your work done, and how much influence you have. Here’s why.

Saves Time

We’ve all been in meetings where someone explains an idea for five minutes and afterward you’re still not sure what they meant. You’re confused about what you’re supposed to do with this information and frustrated that’s five minutes of your life you’ll never get back. Clear communication puts the focus on what matters. For example: You’re working on a new internal process that will speed up client onboarding. Instead of walking your team through every detail, you say: “Here’s what’s changing, why it matters, and how it will save us five hours a week.” Then limit your explanation to just those items. Now they’re with you.

Builds Trust

Presenting ideas well isn’t about being the loudest voice in the room. It’s about demonstrating you did the work. When you share ideas confidently, even in a one-on-one conversation, people take you seriously. The more you know your material and your audience, the less likely you’ll ramble, hedge, or over-explain. For example: You’re proposing a change to your team’s project timeline. You open with: “Here’s what I want to walk you through: the new timeline, what we gain from it, and how it keeps us on track without burnout.” You’re not just suggesting, you’re leading.

Drives Growth

People who communicate well advance their careers faster because they can show the value of what they know. According to a LinkedIn Workplace Learning Report, 92% of talent professionals say soft skills matter as much or more than hard skills. And communication tops the list. For example: You’re up for a stretch role that involves more cross-functional work. If you clearly present your past wins, share your approach, and respond to questions without spiraling, you’re more likely to land the opportunity.

Promotes Buy-In 

You don’t need to be in sales to need persuasion skills. Every time you pitch a new idea, even internally, you’re trying to persuade someone. When you present  well, you make it easy for people to say yes. That often means starting with the benefit to them, not you. For example, the next time you share one of your ideas, say this:“There are three things about this idea that I’m really excited about because they will help us hit our goals faster, save resources, and make things easier for the team.” Then dive into your proposal. Create interest and buy-in from the start.

Improves Results

When you’re boring or confusing, people check out. When you’re clear and direct, they lean in. For example: In a weekly team sync, you summarize a project’s status by saying: “We’re 75% done, we’ve cleared the two biggest obstacles, and we’re on pace to finish two days early.” That gets attention. You  do more than inform, you engage.

Fosters Collaboration

When you present your thoughts clearly, you’re not just sharing your ideas, you’re creating space for others to build on them. For example: You’re brainstorming a solution for a client issue. You say: “Here’s my starting point. It fixes the core issue, works within budget, and gets us to resolution by Friday. Where do you see gaps or better options?” Now your team can focus on refining the solution instead of trying to figure out what you meant. 

How do you effectively present your ideas? Please share in the comments.

Getting in Shape

Photo by Ketut Subiyanto

This week I’m sharing a few questions I’m frequently asked about soft skills. If you feel like you’re managing a team that does what you say but nothing more, you’re not alone. Leading by compliance can get you results. But if you want people to bring their energy, skills, and ideas to the table then you have to inspire them. But how?

Can Soft Skills Be Developed?

Yes, and it takes intention. Think of soft skills like a muscle you have to train. You get better through practice, feedback, and observation. For example, you can learn to listen without interrupting, you can get better at showing empathy, and you can grow more comfortable owning your mistakes.

How Do You Measure Soft Skills?

They’re harder to measure than technical skills, but not impossible. You might track them by asking for 360-degree feedback from colleagues or by reflecting on how people respond to you. Do teammates come to you for advice? Are they honest with you? Do they seem motivated? These signals can tell you if your soft skills are working.

Why Are Soft Skills So Hard To Improve?

Three things: You often don’t get immediate feedback, your habits may be deeply ingrained, and improvement can feel uncomfortable. For example, showing vulnerability takes courage. If you push through that discomfort, you’ll see a huge shift in how your team responds to you. Here are four examples of soft skills and how to start exercising them right away.

Building Kindness

Kindness at work isn’t about being nice for its own sake. It’s about helping people feel seen and supported. Let’s say a teammate misses a deadline. Your gut reaction may be frustration. Instead of acting out of that emotion, schedule a quick one-on-one and calmly ask what got in the way. Maybe they’re swamped or dealing with personal issues. By showing you care, you open the door for a real conversation about workload, priorities, or support. And you send a clear signal that they matter beyond their output.

Building Trust

Trust is about giving others space to do their best work and believing they will. Let’s say you’re leading a project and have a big presentation coming up. A colleague offers to take on a tricky section. Even if you’re tempted to micromanage, you let them own it and you tell them you trust their expertise. That sense of ownership can motivate them to give their best effort, and it frees you up to focus on the bigger picture.

Building Vulnerability

Vulnerability at work is about honesty, especially when it feels risky. Let’s say during a team meeting you share you’re worried about hitting a deadline because of conflicting priorities. Instead of acting like you’ve got it all handled, you invite others to help problem-solve. You’ll be surprised how quickly teammates rally around you when you model openness.

Building Accountability

Accountability means holding yourself, and others, to commitments, while being fair. Let’s say you promise to deliver a report by Friday. Thursday rolls around, and you realize you won’t make it. You send a quick message explaining why and propose a new deadline. That small move shows your team that you don’t sweep things under the rug, and that you respect their time and trust.

What other soft skills would you have included? Please share in the comments.

What Matters?

Photo by The Coach Space


It’s time to rethink your expectations around job benefits. Health insurance, 401(k)s, and Paid Time Off (PTO) used to be standard. Now, they’re negotiable. Rising costs,  shifting priorities, and new work models are changing what companies can offer. What employee benefits can you ask for? Can you design a plan both you and your employer are happy with?

Why Employers Offer Fewer Benefits

Healthcare: Premiums continue to rise and companies are struggling to keep up. Offering comprehensive plans can cost thousands of dollars per employee, per year. Government rules around healthcare, insurance, and employment affect what companies are required to offer.

Profit: Small and midsize businesses may want to provide great benefits but they can’t afford to. Profit margins are tight. Even big companies are watching the bottom line. Short-term and freelance contractors and at-will hiring mean different obligations for employers.

Flexibility: Some employers are moving away from standard plans to offer personalized options: more cash, stipends, or the ability to customize your benefits. A one-size-fits-all approach doesn’t work. Companies are starting to tailor benefits to age, life stage, or role.

How to Rethink Your Expectations

You don’t have to settle for less. But you do need to adjust your expectations based on where you are in life and what matters to you right now.

Evaluate: Ask yourself: Do my benefits expectations match my role, experience, and life stage? For example, moving into leadership might mean shifting from PTO priorities to executive coaching or equity. A new parent might prioritize healthcare over travel perks.

Refocus: Your needs change. What mattered to you when you were 25 years old probably doesn’t matter at 50. Don’t cling to outdated goals. Shift your focus based on what’s useful to you today. 

Traditional Benefits Missing? Ask for These

Education or Upskilling: Ask if they’ll fund certifications, courses, or conference attendance. It helps you grow, and you will use what you learn to help them.

PTO for Mental Health Days: Even if PTO is limited, see if you can take a few days each year to unplug without using vacation time.

Flexible Work Arrangements: If they want you on-site five days a week but don’t offer benefits, ask for a hybrid schedule. Saving time and money on commuting has real value.

Technology or Home Office Stipend: Working remotely? Ask for support with home internet, desk setups, or hardware.

Know What to Ask

Use the conversation to shape the benefits that matter to you. Negotiate for what you need. Be proactive, specific, realistic, and adaptable. Your goal is to satisfy both you and your employer. You won’t know what’s possible unless you ask. Here are some questions you can use: 

  • “Is the benefits package flexible?”
  • “What kind of mental health support is included?”
  • “Do you offer nontraditional perks like student loan help?”
  • “What benefits are included beyond salary?”
  • “What professional development resources are available?”
  • “Can we add a few mental health days or a stipend for leadership training?”
  • “Can you increase base pay or offer a monthly health stipend to offset insurance costs?”
  • “Are flexible hours or hybrid options negotiable?”
  • “Can we revisit the package in six months based on performance?”

What work benefits are most important to you? Please share in the comments.

Quiet Influencer

Photo by Anna Shvets

When you’re looking for a new job, you probably focus on your resume, networking, and interview prep. But there’s another variable quietly influencing your search: your credit history.

Most potential employers can’t see your credit score. This is a numerical rating between 300 and 850 summarizing your credit history. It shows how well you manage debt. 

But potential employers can access your credit report as part of a background check. This is a detailed record of your credit history compiled by credit bureaus like EquifaxExperian, and TransUnion.

Credit information can signal to an employer how responsible you are with money. Late payments, maxed-out credit cards, or unpaid debts may make them think twice about hiring you.

What Employers See

  • Payment history: Whether you pay your bills on time
  • Credit card balances: How much debt you’re carrying
  • Outstanding loans: Student loans, personal loans, car loans, etc.
  • Public records: Bankruptcies, foreclosures, and accounts in collections

Why Employers Check Credit

If a job involves handling money, managing budgets, or accessing sensitive data, a credit check is a tool employers use to assess whether you can be trusted with financial or confidential responsibilities. A history of missed payments or financial trouble may be interpreted, fairly or not, as a sign you make poor decisions under pressure. 

If you’re going for a position at a financial services company, then expect to get your credit report pulled. But any employer can include a credit check as part of a background screening.

How It Can Affect Your Job Search

Let’s say you’re applying for a role at a mid-size tech company as an operations lead. You’ve got a great resume and solid experience. But the role also involves managing budgets and vendor payments. If the company runs a credit check and sees you have a recent bankruptcy, it could lead to doubts about your financial reliability. This doesn’t automatically mean you’ll be rejected. But if the hiring manager is weighing two qualified candidates, your credit history could become a deciding factor.

You Have Rights

If a company plans to check your credit as part of a background screening, they must ask for your written permission first. If they decide not to hire you because of what they find in your credit report, they must notify you. You also have the right to know which report they used (Equifax, Experian, or TransUnion), review it for errors, and dispute any inaccuracies so this won’t happen the next time you apply for a job.

What You Can Do Now

It’s not time to panic, but you do need to be aware of what’s on your credit report. Here are three things you can do today:

Check: Go to Annual Credit Report.com. You’re entitled to a free report from each of the three major credit bureaus (Equifax, Experian, and TransUnion) once a year. Check for errors, outdated info, or accounts you don’t recognize.

Improve: If you spot missed payments or high balances, prioritize making payments on time and pay down debt. Even small progress shows financial responsibility and may help your case if you’re asked about it during the hiring process.

Rehearse: If you know your credit history could raise red flags, prepare a brief, honest explanation. For example: “A few years ago, I had a medical emergency that affected my finances, but since then I’ve been steadily rebuilding and haven’t missed a payment in over 18 months.” This keeps the focus on how you took responsibility and what steps you’re still taking to improve. 

How do you feel about the impact of your credit history on your career? Please share in the comments.

The Discomfort Zone

Photo by Kampus Production


Every day you show up, log in, and face a mix of meetings, messages, and missions. One part of your brain is ready to tackle the day. Another part is whispering you’re not cut out for this, you’re falling behind, or someone is going to realize you don’t actually know what you’re doing. The hardest work isn’t always on your to-do list. Sometimes, it’s in your head.

Take Action

You’ve probably heard of Impostor Syndrome. It’s the feeling you’re one mistake away from being found out. SPOILER ALERT: Everyone is an impostor. No one knows everything. Successful people keep moving in spite of their fear. Let’s say you’ve been asked to lead a project that feels a little too big. You tell yourself someone else would be more qualified. You consider turning it down or waiting for a time when you feel more ready. That feeling you interpret as a red flag is actually a sign you’re growing. Don’t wait for it to disappear. Step forward and get past it. The next time you feel like an impostor, say this to yourself, “I feel uncertain, but that doesn’t mean I’m not capable.” Then take one small action: Send the kickoff email. Ask a question. Book the meeting. Build momentum before doubt has time to settle in.

Awkward Practice

Instead of comparing yourself to your coworker who seems to always have it all together, ask yourself, “Am I better today than I was yesterday?” Growth usually isn’t a big leap. It’s a series of small shifts. Let’s say you struggle with leading meetings. You freeze under pressure or feel awkward when the discussion goes off-track. Instead of waiting to magically become more confident, rehearse a few common scenarios. Script a few go-to phrases you can fall back on like: “Let’s pause for a second. What’s the main decision we need to make here?” Or “That’s a good point. How do you see that impacting the timeline?” Practice these out loud. When the moment comes, your brain won’t scramble for words because it will already have them. Also, when something feels uncomfortable or new, ask a curious question instead of retreating. For example: Instead of saying, “I don’t know how to do this,” try, “What’s the first thing I’d need to understand to make progress?” Curiosity shifts you from panic to problem-solving.

Be Brave

Scroll through LinkedIn and you’ll see perfect projects, prominent prizes, and polished personal brands. But you’re not seeing the stress, the edits, or the three failed drafts behind those posts. If you’re holding back at work because you’re worried about not having all the answers, that’s normal. But if you let that fear guide your decisions, you’ll stay stuck. To be productive you have to be brave enough to make mistakes out in the open. Let’s say you’re in a team meeting and someone suggests a direction you’re not sure will work. You have an idea, but it’s not fully formed. You can either stay quiet or speak up, knowing you may be wrong. Say something like: “That is very interesting. We should definitely consider that. And it makes me wonder (Insert the thing you’re wondering here.) Would that work?” You’re not pretending to be the expert. You’re starting a new conversation. That’s valuable. Also, give yourself permission to say, “I don’t know, but I’ll find out.” You build trust by owning your gaps instead of pretending you don’t have any.

How do you move through your discomfort zone at work? Please share in the comments.

Dark Empathy

Photo by Yan Krukov

A volunteer and I were troubleshooting the usual challenges an event brings when I said, “Misery loves company.” Without missing a beat, they replied, “Don’t be a misery partner.” This gave me pause. I wasn’t just expressing dissatisfaction. I was inviting someone into it. Is that the right thing to do? Misery loves company, but do you have to RSVP? 

What It Really Means

You’ve probably heard the phrase before, but let’s be clear: “Misery loves company” means that unhappy people often look for others to share in their pain. Sometimes it’s about validation,“You feel this too, right?” Other times it’s darker. If someone is stuck in a bad mood it can feel comforting to pull others into the same mindset. Misery doesn’t just want to be seen. It wants companionship.

Why We Do It

Validation: Misery can feel isolating. Sharing it with someone makes it feel less lonely.

Mood-matching: If you’re angry or disillusioned, it can feel easier if the person next to you is too. Misery becomes a shared lens.

Identity Reinforcement: If you stay in that space long enough, you begin to expect and even seek out negative experiences. It becomes part of how you navigate work and relationships.

When It Becomes a Problem

In the short term, it feels good to vent. It builds rapport. It can even feel productive. But over time, it shifts from bonding to spiraling. For example: Let’s say you have a coworker who habitually wants to talk about how bad leadership is. Every team meeting, every direct message, it comes up. At first, you agree. But soon, you’re both repeating the same frustrations. Nothing changes. The venting doesn’t lead to clarity or action just mutual grievance. That’s misery partnering. When two or more people reinforce each other’s worst perspectives, you’re no longer helping each other process. You’re keeping each other stuck.

How to Spot It at Work

Misery partnering isn’t always loud. It can look like two coworkers grabbing coffee just to complain. It can happen in team group chats or in “just being real” sidebars. It drains your energy and clouds your decision-making. When your default mode is skepticism or complaint, even good ideas start to feel naive. You stop contributing. You play it safe. You protect your mood instead of doing your best work. If you experience any of these, then ask yourself:

  • Am I sharing this to feel better, or to feel right?
  • Does this conversation go in circles?
  • After we talk, do I feel lighter or more stuck?
  • Are we taking any action, or just blaming?

What You Can Do Instead

You don’t have to cut off every frustrated coworker and you don’t have to bottle things up. You do need to be mindful about how much airtime you’re giving to frustration and whether it’s helping. The next time a coworker starts spiraling, don’t pile on. Listen, but then steer. Ask what they need. Suggest one step forward.

Start with this mantra, “I can listen without absorbing. I can empathize without enabling. I can share my own frustrations without needing someone to sink with me.” Call it what it is: a moment, not a mindset. If you catch yourself being the one pulling others in, pause and ask yourself: “What do I actually want right now? Validation? Change? Relief?”

If you’re stuck in a loop with someone who’s always venting, try asking: “What are you thinking about doing next?” It’s a gentle nudge out of rumination and into action.

How do you avoid becoming a misery partner at work? Please share in the comments.

Take the Time

Photo by Vitaly Gariev

You take time off work for a vacation because it’s a culturally acceptable reason to rest and restore your body. But what about your brain? If your mind is overloaded, your work suffers. In conversations about taking a mental health day, I’ve heard opinions running the gamut from eye rolls  to enthusiasm. Of course, this made me curious.

Why Take a Mental Health Day?

It’s like resting a strained muscle. Pushing through the discomfort doesn’t make you tougher, it wears you down. If you’re feeling mentally exhausted, overwhelmed, or unmotivated, this shows up in your work through mistakes, slow responses, or irritability. Would you trust your job performance after three nights of bad sleep and three days of nonstop Zoom calls? If you catch yourself zoning out in meetings, dreading small tasks, or struggling to care about the outcome of your work, it’s time to step away and reset. How often you take one depends on your workload. Does it regularly drain you? Then maybe quarterly is a good cadence. Do you usually need a break after an intense project? Then schedule one for immediately after delivery. Create a personal system that accommodates the pace of your work and makes it sustainable.

How Do You Request One?

Some people I spoke with worried taking time off for mental health would make them appear unreliable or weak. The good news is more organizations recognize that productivity depends on sustainable work habits. Unlike calling in sick with the flu, a mental health day is best planned ahead. Choose a day that doesn’t interfere with deadlines, major events, or key meetings and give your manager as much notice as possible. Communicate clearly and keep the focus on coverage and continuity.

If your workplace is supportive: Be direct. For example say, “I’d like to take a mental health day next Friday. I’ll make sure everything is on track before I’m out, and I’ll loop in [Teammate] on anything that might come up.” After your manager approves it, coordinate coverage of your projects. Let coworkers know who to contact while you’re out and make sure that person has all the resources they need. Offer to return the favor when they take a day off.

If not: Be indirect. Label your request the term your company uses for flexible paid time off. Usually it’s called a personal day or a vacation day. You don’t have to explain how you intend to use it. For example say, “I’d like to request a personal day for Thursday. My workload is covered and I’ll be back Friday.”

What Should You Do on One?

Nothing: Turn off your laptop. Watch a show. Lie on the couch. Do not feel guilty.

Spend time with people you like: Meet a friend for coffee or lunch. Visit a sibling. Talk to someone who doesn’t expect work talk. Social connection lowers stress and boosts mood.

Roam if you want to: Take a long walk, go to a hot-yoga class, or bike around your neighborhood. The goal is to boost your energy not your fitness.

Something just for you: Read a book. Cook a slow meal. Run errands you’ve been avoiding. Clear clutter. Anything that restores your sense of control.

Volunteer: Spend an hour helping someone else. This could be anything from packing food at a local pantry to helping a student learn to read. There are many local nonprofits who need help.

What is your take on a mental health day? Please share in the comments.

That’s Another Good Question

Photo by rawpixel.com

After last week’s article about good questions, the “Is It Worth Your T.E.A.M.” community had some good questions for me! I’m sharing them, along with examples, for the good of the group.

Common Question Concerns

How do you ask a technical question without sounding naive?
Focus on what you need to learn, not what you think you should already know.

  • “I’m still getting familiar with this. Will you please walk me through how it connects to X?”
  • “What’s the best resource to understand how this works?”

How do I ask my manager better questions during one-on-ones?

Ask about expectations, priorities, and growth. Avoid general “How am I doing?” questions. Be specific.

  • “What’s one area you think I could improve in this quarter?”
  • “Are there upcoming projects where I can take more ownership?”

How can I ask questions in a meeting without sounding like I’m showing off?
Focus on curiosity, not performance. Keep it brief, stay on topic, and avoid jargon.

  • “Will you please share the process of how you weighed the options before landing on this approach?”

How do I ask questions without putting someone on the spot?
Use softer language and offer space to think. This shows respect and lowers pressure.

  • “Would you be open to breaking down how you landed on this course of action?”
  • “Whenever you have a moment, I’d love your take on how this decision came together.”

How do I push back or ask challenging questions tactfully?
Lead with respect and aim for understanding, not debate.

  • “I see the benefits of this plan. What would you say are the trade-offs we should keep in mind?”
  • “Is there a reason we ruled out Option B? I just want to understand the full picture.”

What if I asked a question and it didn’t land well?
It happens. Don’t over-apologize. Clarify or follow up later.

  • “I realized I may not have been clear earlier. What I meant to ask was how the timeline impacts our testing phase.”

How do I ask better questions in time-pressured situations?
Be direct and results-focused. You don’t need context, just the information you need to act.

  • “Can I get a quick yes/no on whether we’re moving forward with the update today?”
  • “Is this blocking anything else on your end?”

How do I know when to stop asking questions?
Watch for signs like:

  • You’re getting short answers
  • The person repeats themselves
  • The person says, “Let me follow up later
  • You’re starting to ask things you could find yourself

At that point, pause, thank them, and pivot:

  • “Thanks, that’s helpful. I’ll take a look at what’s documented and come back if needed.”

Practice

Asking good questions helps you make better use of your time, understand your work more clearly, and build stronger relationships. Like any skill, it improves with practice. Here are a few things you can do right away:

  • Rewrite one vague question you ask often. Make it clearer and more specific
  • During your next meeting, ask one thoughtful follow-up
  • Practice active listening: Summarize what you heard before asking a follow-up
  • Ask one question at a time
  • After a presentation, ask a “what’s next” question to keep things moving

Do you have a good follow-up question for the community? Please share it in the comments.