As holiday season is upon us, we did a Session on how to prepare for it. Karolina Šilingienė and Luis Felipe Mohando from Crespect, an Estonian legal tech company, addressed a challenge familiar to lawyers worldwide: how to actually disconnect and enjoy holidays without constant fear of client emergencies or administrative chaos. Their insights reveal that whilst technology can help, successful time off ultimately requires human planning, clear processes, and cultural change within law firms.
The Guilt-Driven Laptop Holiday Problem
The speakers opened by acknowledging a common scenario: lawyers who bring laptops to paradise islands, spending supposed holidays inside hotel rooms rather than enjoying their destination. This behaviour stems from justified guilt, as Mohando explained: “We are famously flying by the seat of our pants. We are very diligent with our matters, but in terms of internal matters, organising the law firm, people are not that diligent.”
This creates a vicious cycle where neglected administrative tasks accumulate throughout the year, requiring frantic last-minute attention before departure. “All the administrative things that you neglected during the year now you have to do them all at once in the last week,” Mohando noted. The inevitable result is either incomplete preparation or bringing work on holiday as insurance against potential disasters.
However, the speakers argued this represents mismanagement rather than inevitability. The solution lies in better systems, processes, and advance planning rather than accepting perpetual availability as a professional necessity.
The Human Element: Planning Over Technology
Šilingienė emphasised that technology alone cannot solve the holiday problem: “If everyone’s expecting a silver bullet or that AI will help them somehow have better vacation, I don’t wanna spoil it, but no, it’s not. It’s a human thing. You need to plan your vacation.”
This preparation should begin weeks rather than days before departure. Their recommended approach includes:
Three weeks out: Review deadlines, core dates, and urgent tasks. Use practice management systems to identify what requires immediate attention, what can be delegated, and what can wait.
Administrative cleanup: Finalise time entries, complete draft invoices, and clear accumulated backend work that typically gets postponed during busy periods.
Team coordination: Check colleague availability to ensure backup coverage exists. “You don’t want a client receiving an out of office email saying that someone will read this email, but then that someone is on vacation,” Šilingienė noted.
Client communication: Proactively inform clients about upcoming absence, provide alternative contacts for urgent matters, and frame communication positively as relationship maintenance.
Technology as Enabler: Data Accessibility and Process Automation
The speakers positioned technology as a facilitator for better holiday preparation rather than an automatic solution. Their practice management software addresses several key areas:
Data accessibility: Ensuring colleagues can access case information, deadlines, and client details when covering for absent lawyers. This transparency reduces dependency on any single individual.
Delegation systems: Technology can help identify who has appropriate skills and availability to handle specific matters, but cannot replace human judgement required for effective delegation.
Process automation: Routine administrative tasks can be systematised, reducing the last-minute scramble that creates holiday anxiety.
However, Mohando emphasised the importance of clean foundational data: “You need to have clean and actionable data that is reliable. If you are just incorporating AI on top of faulty data, then you will get faulty outputs.”
Scaling Communication in Larger Firms
The speakers identified particular challenges in larger organisations where vacation planning becomes opaque. “The bigger the organisation is, the more difficult it is to track what is going on in the different teams,” Mohando explained. “Very often, lawyers just arrange their leave with their immediate supervisor, and that stays there between the two.”
This creates information silos where colleagues remain unaware of others’ vacation plans, leading to dreaded chains of out-of-office responses. Their solution involves centralised but accessible information about colleague skills, availability, and vacation schedules—creating a “colleague list” that functions beyond a simple contact directory.
Turning Holidays into Business Development Opportunities
An interesting dimension involves leveraging travel for relationship building. Mohando shared his practice of contacting professional contacts when visiting their cities: “Everybody is very happy to meet you if you happen to visit their countries.”
This transforms travel from purely personal time into hybrid opportunities serving both relaxation and professional development. Their CRM system specifically tracks international relationships to facilitate such connections, allowing lawyers to identify business development opportunities in vacation destinations.
The Nordic Model and Client Expectations
The speakers, based in Estonia, provided perspective from a region with different cultural expectations around vacation time. Šilingienė described the Baltic approach: “July in Europe, it’s like where the cities are empty, the beaches are full, and your emails just go somewhere into the void.”
Regarding client expectations, both speakers suggested lawyers often create unnecessary pressure. “Clients definitely appreciate, and sometimes they don’t really need the answer as urgent as lawyers wouldn’t anticipate,” Šilingienė observed. “Sometimes we’re putting ourselves in a corner where it’s not actually needed.”
Effective client communication involves informing them about upcoming absence whilst providing appropriate alternatives. “Just give them options, raise awareness, inform them about the vacation and no one will freak out,” Šilingienė advised.
The Burnout Prevention Imperative
The discussion turned on concerning industry statistics. “According to recent studies, over 70% of lawyers have experienced burnout symptoms—exhaustion, cynicism, reduced effectiveness,” Šilingienė noted. This creates a business case for supporting genuine time off rather than token breaks interrupted by work.
The concept of “offline is the new luxury” reflects recognition that true recovery requires genuine disconnection. Firms that support such disconnection benefit from more productive, creative, and resilient lawyers upon return.
Beyond Individual Responsibility: Institutional Change
Whilst emphasising individual responsibility for vacation planning, the speakers highlighted institutional obligations. Šilingienė suggested: “If your firm does not have a checklist, if your firm does not have a delegation rule system in place, maybe that’s an issue worth raising.”
Effective vacation policies require clear delegation procedures, transparent availability tracking, cultural support for genuine disconnection, process documentation enabling seamless handovers, and technology infrastructure that facilitates rather than complicates time off.
Proactive Planning NOT Reactive Crisis Management
The overarching message emphasises proactive planning over reactive crisis management. Rather than accepting that holidays will inevitably involve work interruptions, lawyers can create systems enabling genuine disconnection.
As Šilingienė concluded: “Don’t wait for exhaustion to force you to stop. Take a break now.” This requires shifting from viewing vacation as a luxury requiring guilt and compromise to recognising it as a professional necessity deserving proper planning and institutional support.
The combination of individual preparation, technological enablement, and cultural change can transform holidays from stress-inducing ordeals into genuinely restorative experiences. For legal professionals approaching summer holidays, the message is clear: start planning now, use available technology to streamline preparation, communicate proactively with clients and colleagues, and recognise that taking proper time off is a professional responsibility rather than personal indulgence.
