You are receiving this email because you either created a WorkTogether Talent Consulting (formerly WorkMonger) Career Platform Account,
applied to a job opening at one of our client organizations, or registered directly to receive Leaders in Education.
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A Publication of WorkTogether Talent Consulting (formerly WorkMonger)
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As you apply for jobs, some applications make cover letters optional. Our advice? Always follow directions—if it's required, submit it. If it's optional, use a cover letter to provide context your resume can't: personal connections, career gaps, expertise examples, or why you're switching industries. Submit one when extra context helps, skip it when it doesn't.
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The 2026 job market is unforgiving, and most job seekers are unprepared. This piece delivers hard truths: applying online like it's 2005 won't work, entitlement kills opportunities, and employers hire quantifiable results, not opinions about yourself. Clean up your digital footprint, speak in numbers, and position yourself strategically. Intentional preparation matters more than ever.
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What We’re Writing Right Now
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If job searching feels harder right now, that’s because it is! More workers are hunting in 2026, but competition is intense - 68% expect longer searches than before. Pain points include too many applicants per role, skills mismatches, and complex hiring processes. You're not imagining it. The market is tough, and strategic applications are essential!
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Career Corner: Ask a Recruiter
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How to ask questions of hiring teams in interviews that will give you thoughtful answers
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“What questions should I ask at the end of my interview?”
My clients who ask for this support are usually inspired by two things:
- Impressing the hiring team with their insightful and strategic questions.
Or
- Avoiding a bad fit, especially because they feel they missed out on detecting obvious red flags with other employers.
Let’s focus on the latter for today - avoiding red flags.
First off, you can ask THE BEST questions EVER, but you can’t control for the following: how transparent the hiring team is willing/able to be, or how self aware they are about the topic (the culture of the organization or team they lead, their management style, etc).
Assuming you are interviewing with someone who has some self-awareness, and is able to be transparent if asked direct questions about particular topics, here’s how I encourage clients to approach developing questions:
- Reflect on your own red and green flags for the following areas (this is not comprehensive, but can give you a good start): team culture, conflict at work, your manager’s management style, learning & development, strategic planning, how goals are developed/tracked/used, performance management, office politics, work schedule, internal communication, how “authenticity” is defined, boundaries between personal/professional, taking time off, etc.
- During the interview process, you’ll want to listen for examples of those green flags and red flags. After each conversation you have with the hiring team, reflect on where they’ve shared insight and actual examples, and where they still haven’t shared context (for example, they might provide ample examples of the role that strategy, data, and tracking play at work and ask you to complete a performance task using their framework and then debrief the experience with you - that would be a good way to get a sense of how they approach strategy/planning/tracking without you having to ask).
- Identify 2-4 focus areas that you hope to explore with the hiring team in your final interview Q&A, or if you’re offered the job. For example, learning how leadership navigates conflict among their executive team, or a manager’s management style. Instead of asking “how do you navigate conflict as a team?” instead ask “What’s a recent strategic decision that inspired friction/conflict among your team? How did you all navigate the conflict?” Asking for actual examples will provide you a more clear picture of actual style and approach. Ask a generic question, expect a generic answer.
- If offered a position, always ask if you can speak to a couple internal folks before making a final decision. These could be peers on the team you’re joining, or peers who are on other teams.
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TrulyHired - An Educational Equity-Focused Job Board
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Since 1997, Mass Insight has been a valued partner to schools, districts, and state education agencies. They are looking for a Managing Director of Business Development who will serve as a senior leader accountable for Mass Insight's earned (fee-for-service) revenue by securing and expanding partnerships with schools, districts, and state education agencies. The ideal candidate has a demonstrated success meeting or exceeding earned revenue targets through consultative sales and business development in education, nonprofit, or professional services environments. Deep knowledge of the K–12 education landscape, including current system needs, policy and funding dynamics, and relevant trends; experience in or familiarity with priority states preferred (PA, IN, RI, MA, CO).
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Equitable Facilities Fund (EFF) is a nonprofit social impact fund that’s on a nationwide mission to help high-performing public charter schools spend more money on students and less on the costs of borrowing for their facilities. EFF is looking for a new School Lending and Outreach Associate, who will play a critical role in building the pipeline and portfolio of schools seeking EFF financing, and amplifying our efforts to ensure all high-impact schools in historically marginalized communities have a pathway to affordable facilities. The ideal candidate has 2+ years of professional experience in charter school operations, real estate advisory, mission-oriented lending, non-profit finance, or investment banking.
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TrulyHired is a quick, easy, and tailored job board that specializes in providing job seekers with educational equity roles at impact-driven education organizations. Here are a few of the amazing jobs we have available. Check them out and apply if you're interested!
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You don’t have to be a job seeker to take the next step in your professional growth.
Our tailored career services—like resume reviews, interview prep, and personalized coaching—help leaders like you gain clarity, align with your goals, and stand out.
Ready to level up?
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You are receiving this email because you either created a WorkTogether Talent Consulting (formerly WorkMonger) Career Platform Account, applied to a job opening at one of our client organizations, or registered directly to receive Leaders in Education.
Don't want to hear from us? Let us know by clicking here.
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