As a DM of a 4-player group, would it be appropriate for me to run a private 1-on-1 session so that one PC can act secretly?

Question

I'm currently running a campaign with a fairly typical group of 4 players. Everyone gets along pretty well, however one of my player's Rogue has been struggling to find his niche in the party. To remedy this I had an NPC secretly give him a thief/spy "quest" for him to complete with or without help from the others.

The player took to this pretty wholeheartedly and has come up with an elaborate plan that he intends to execute alone while the other PCs sleep. He also wants the quest to remain secret from the PCs. I'm excited by the prospect of him finally having a unique role, and I think that there will be some interesting encounters, however I'm worried that it'll be boring for the other players to watch him play out his plan over the course of an hour or so.

Would it be appropriate for me to run a one-on-one session, just me and the Rogue?

I'm just worried that a) the other players will feel neglected and b) that they'll feel blindsided by any potential impact this quest has on the campaign's progression.

Answer 1

If possible, run the side session on another time or day with just those participating

We've actually done this a number of times in a campaign I'm playing in. The players or DM occasionally come up with side quests relevant to a select few players, who we then find a time to play through an another day of the week. This prevents it from disrupting the group as a whole by keeping them from playing, while allowing for the side-quest to still take place.

The smaller group also helps the interaction go much faster. One session was literally the DM and I on a 15 minute car ride, playing in the theater of the mind. Another one was just my coming along to assist on another player's side quest, and only took us half an hour. Yet another of mine took about an hour, and was very similar to what you described above (me, the rogue, on a secret thieving quest).

So yes, this is entirely possible and normal. As I mentioned above, just do your best to avoid disrupting the other players, either by making them sit through it, or by making them have to skip what would have normally been a group session altogether.

Be aware though that by allowing this for one character, it may open up the door for others to request the same. This doesn't mean you have to oblige, especially if you only intended this to be a one-off opportunity for help the other player connect to their character better. But be prepared to know how you intend to respond and handle such requests.

Impact to the main story

This part is a little more dependent on you as the DM, and how you want this to affect your world. In the same way that backstories can (and should) affect the overall plot to increase character engagement, so can and should present stories. Ideally you might want to avoid consequences that take agency away from other players in their part of the story, but that doesn't mean it can't be relevant.

For example, in my thieving side quest I mentioned above, completion of the task got me into a city-wide underground criminal network. This allowed me to help other members of my party as an informant, who could get information on quests and goals we as the whole party sought, and helped increase our group dynamic. This had an affect on the story by helping to improve my investment in it and provided another resource for the other players, but didn't take anything away from the others.

Side-note: Handling XP

As NautArch suggested in a comment below, one thing to keep in mind is how this might affect XP gain. Depending on what method of leveling you use (standard XP, milestone, 3 pillar, etc), you will want to be careful that these side quests don't give someone an unfair lead over their fellow players. In our campaign, side quests typically only granted XP to those who were behind the others, often with the quest itself being an intentional way for that player to catch up.

As someone who typically attended every session and was at the lead in XP, I would often agree with my DM to forgo it altogether in order to simply enjoy the adventure, or in other cases would join on someone else's side quest (if they were ok with it) as a way to help them level their character faster. Again, this will all depend on your group and how leveling works, but so long as the side quests aren't giving them an unfair/special advantage, you should be good.

Answer 2

There are pros/cons to both options

Your concerns are legitimate; I have experienced exactly those issues in the past.

I went into a lot of detail on the pros and cons of running private scenes in my answer to a related question on dream sequences. In that answer I argued that is comes down to a choice between meta-gaming and trust, and which is more important at your table. Running things openly promotes trust but can lead to meta-gaming, and vice versa for keeping things secret.

Your situation is slightly different given that you are talking about an entire session rather than just a scene or two. I encountered a similar situation where two of my players ended up in prison with the rest of the party outside. I choose to run two separate session for the split party and learned the following lessons.

1. The players didn't want the non-playing players watching. I had initially suggested that they could come if they were curious. All players however, preferred to keep their session private. Your mileage may vary here but this was my experience.

2. There are information gaps in the party. I didn't recognise this at the time but it has come up a few times since. Things happened during those sessions that had an ongoing impact in the campaign. NPCs they met, things that players did, etc... It has become clear that having players missing means not everyone knows the information.

   There are certainly advantages to this; the players are unable to meta-game based on knowledge their character doesn't have. However, there are disadvantages too, in that some important details were forgotten by the main note-taker only being present in one session.

3. Important character growth wasn't shared. One of the characters was deeply affected by the events that occurred during their session. They have used this to change the way they behave going forward. The players that were not present question the changed behaviour since they don't fully understand the motivation. This has led to issues (now resolved) for that player where they considered retiring the character.

How does all this apply to your situation?

There are a number of advantages to running a one-on-one session for that player. The session will run faster, be more immersive and provide opportunities for things you couldn't do with the entire party.

At the same time, you need to consider how this will impact the other members of your party. Will there be trust issues with the rogue doing things behind the party's back? Could they feel like they have missed out on something important? Or worse, that you are playing favourites?

There is only one way to know the answer, and that is to talk to your players. Ask them what they want to do and how they feel about it. Armed with that information, you can then decide how to approach this session.

Answer 3

Both the game I play in and the one I DM do this pretty frequently; however, we primarily do it via a chat client called Telegram. It has a client for Android, iOS, Windows Phone, Windows/Mac/Linux, MacOS, and a browser-based web client. You can create chat rooms and invite a dice-rolling bot, so you can even have them roll dice remotely.

This works well for one character I have who is part of a secret division and often times sneaks out in the night to get intel or orders from his affiliates.