Starting Monday
Practical guidance for C-suite technology executives in active search, and the coaches, search firms, and advisors who work with them.
Every article should help you decide whether Starting Monday solves your next step. If the post is useful, the next click should be the demo or the pricing page, not another blog post.
May 15, 2026 · 6 min read
Most executive candidates still position around tenure and title. Hiring teams at the C-suite and VP level screen for transformation evidence, cross-functional influence, and business outcomes. Here is what the data says.
Read →May 15, 2026 · 6 min read
Strong candidates are often ignored for reasons that have little to do with capability and everything to do with decision pressure. The frame you use in outreach can reduce that pressure and increase response rates.
Read →May 15, 2026 · 5 min read
C-suite and VP searches are won on specificity, timing, and preparation quality. We built Starting Monday to replace generic templates with role-specific positioning and high-context execution.
Read →May 13, 2026 · 6 min read
A transparent look at our methodology: how we define event dates, posting dates, lag windows, and the primary sources we use to estimate early executive-role timing signals.
Read →May 12, 2026 · 6 min read
The strongest executive candidates run a disciplined daily operating rhythm: signals, targeted outreach, prep, and follow-through. Here is the exact routine and the weekly metrics that keep momentum high.
Read →May 6, 2026 · 6 min read
Most technology executives think about executive search firms the wrong way. Here is how retained search actually works, what gets you on the short list, and why timing matters more than almost anything else.
Read →May 6, 2026 · 5 min read
The honest answer most people do not say out loud: six to eighteen months. The range is that wide for a reason, and where you land in it depends on decisions you make before you start.
Read →May 7, 2026 · 5 min read
The VP-to-CIO move is not a promotion. It is a repositioning. What changes in the CIO seat, what search firms look for, and how to build the case before the search starts.
Read →May 10, 2026 · 7 min read
Real data from monitoring hundreds of company career pages across technology-intensive sectors. What the C-suite job market looks like in Q2 2026, which signals precede a search, and how to monitor career pages before roles appear on LinkedIn.
Read →May 7, 2026 · 5 min read
CISO interviews test something most security executives are not trained to do: explain risk in business terms to a room that does not think in frameworks. Here is how to prepare for the conversations that actually matter.
Read →May 7, 2026 · 5 min read
Most CDO job descriptions tell you what the company wants you to do. Very few tell you what they actually need. The gap between those two things is where most CDO searches go wrong.
Read →May 7, 2026 · 6 min read
The compensation conversation for a C-suite role has a different structure than every negotiation you have had before. What to know before the offer, how to read the room, and where most executives leave money on the table.
Read →May 8, 2026 · 5 min read
The board presentation is not a technology briefing. It is a risk and value conversation. What the board actually wants to hear in the first ninety days, and how to walk in ready.
Read →May 8, 2026 · 6 min read
PE-backed companies hire C-suite leaders for a different reason than public companies do. The mandate is tighter, the timeline is compressed, and the equity is structured around an exit. What you need to know before you take the call.
Read →May 8, 2026 · 5 min read
Most executive resumes are read by a search firm associate before they reach a partner. Here are the gaps that filter candidates out before the first conversation and how to close them.
Read →May 8, 2026 · 5 min read
Retained search firms work for the client, not the candidate. Understanding how they actually operate changes how you manage every relationship and every search.
Read →May 10, 2026 · 6 min read
The fastest C-suite searches start with a list. Not of job openings. Those are late. A list of forty to sixty companies you would say yes to before the offer is made. Here is how to build it, what to put on it, and what to watch for once you have it.
Read →May 11, 2026 · 5 min read
Most technology executives spend their career in one seat without seriously considering whether the other fits better. The CIO drawn to product strategy might be a natural CTO. The CTO frustrated by ambiguity might be a natural CIO. Here is how to tell.
Read →May 11, 2026 · 6 min read
Most technology executives reach for the title with more letters. That is the wrong frame. The real question is which role matches how you create value and what kind of work makes you excellent.
Read →May 11, 2026 · 5 min read
Ask companies how long a CTO search takes and they will say 8 to 12 weeks. Ask candidates and the honest answer is very different. What determines where you fall in the range and what you can actually control.
Read →May 12, 2026 · 6 min read
LinkedIn is the only professional platform where your most important future employers spend time. Used well, it builds inbound interest without looking like you are searching. Used poorly, it is a credibility liability. Here is the difference.
Read →May 12, 2026 · 5 min read
Not job boards. Not LinkedIn Easy Apply. Not cold-emailing recruiters. Here is how CIO roles are actually filled and what that means for how to run your search.
Read →May 10, 2026 · 7 min read
The CTO role has no agreed-upon definition. Before you can build a target company list, you have to decide which version of the CTO you are building toward. That decision shapes every other part of the search.
Read →May 10, 2026 · 7 min read
On the day your CIO role ends, you become your own organization: a one-person company with no revenue, no runway, and no manager. Most executives are not prepared for this. Here is what changes when you treat the search like a business.
Read →May 10, 2026 · 6 min read
Most executive coaches underestimate how much of the search happens outside the session. Here is what changes when your clients have the right infrastructure.
Read →May 11, 2026 · 6 min read
Most of what you know about running a job search stops working at the senior executive level. The rules are different, the timeline is longer, and the preparation standard is higher. Here is what actually changes.
Read →For coaches, search firms, and advisors
May 11, 2026 · 6 min read
Most executive coaching practices are strong on strategy and weak on infrastructure. The gap shows up in first-round interviews, stalled pipelines, and sessions that spend too much time on context. Here is what changes when you fix it.
Read →May 11, 2026 · 6 min read
Technology executive searches run longer and require different support than general executive outplacement. What CHROs can do to improve outcomes for CIOs, CTOs, and VPs of Technology in transition.
Read →May 11, 2026 · 5 min read
The most common reason a technology executive candidate does not advance past the first round is not fit. It is preparation. What adequate preparation looks like at the senior level, and what search firms can do about the gap.
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